Table 1.
Synthesis of olanzapine (2) and quetiapine (3).
| No. | Substrates | Molar ratio | Process conditions | Power [W] | Reaction conditions | Time | Yield % | |
|---|---|---|---|---|---|---|---|---|
| 1 | 4 | 5 | 1 (4): 2.4 (5) | conventional, - 10 °C | – | THF, Et3N | 4 h | 82 (Mesar et al., 2008) |
| 2 | 4 | 5 | 1 (4): 2.4 (5) | conventional, - 15 °C | – | THF, NaOH | 4 h | 98 (Mesar et al., 2008) |
| 3 | 4 | 5 | 1 (4): 2.4 (5) | conventional, - 10 °C | – | THF, NaH | 3 h | 98 (Mesar et al., 2008) |
| 4 | 4 | 5 | 1 (4): 2.4 (5) | conventional, - 10 °C | – | THF, t-BuOK | 2 h | 98 (Mesar et al., 2008) |
| 5 | 6 | 7 | 1 (4): 1.3 (5) | conventional, 115–120 °C | – | n-butanol, Na2CO3, NaI, TBAB | 24 h | 60 (Diller et al., 2004) |
| 6 | 6 | 7 | 1 (4): 1.3 (5) | conventional, 115–120 °C | – | toluene, Na2CO3, NaI, TBAB | 24 h | 72 (Diller et al., 2004) |
| 7 | 6 | 7 | 1 (4): 1.3 (5) | conventional, 100 °C | – | water, Na2CO3, NaI | 9 h | 80 (Ashok et al., 2006) |
| 8 | 4 | 5 | 1 (4): 1.5 (5) | Ultrasound Bath, Frequency 40 kHz, continuous | 80 | DMFa, K2CO3, TBAB | 60 | 40 |
| 9 | 4 | 5 | 1 (4): 1.5 (5) | Ultrasound Bath, Frequency 40 kHz, continuous | 80 | DMF, K2CO3, TBAB | 1 h | 44 |
| 10 | 4 | 5 | 1 (4): 1.5 (5) | Ultrasound Bath, Frequency 40 kHz, continuous | 80 | DMF, K2CO3 | 2 h | 15 |
| 11 | 4 | 5 | 1 (4): 1.5 (5) | Ultrasound Bath, Frequency 40 kHz, continuous | 80 | CH3CNa, K2CO3,TBAB | 1 h | 67 |
| 12 | 4 | 5 | 1 (4): 1.5 (5) | Ultrasound Bath, Frequency 40 kHz, continuous | 80 | CH3CN, K2CO3, TBAB | 1 h | 49 |
| 13 | 4 | 5 | 1 (4): 1.5 (5) | Ultrasound Bath, Frequency 40 kHz, continuous | 80 | DMFa, Na2CO3, TBAB | 1 h | 50 |
| 14 | 6 | 7 | 1 (6): 1.5 (7) | Ultrasound Bath, Frequency 40 kHz, continuous | 80 | DMF, K2CO3, TBAB | 2 h | 72 |
| 15 | 6 | 7 | 1 (6): 1.5 (7) | Ultrasound Bath, Frequency 40 kHz, continuous | 80 | CH3CN, K2CO3, TBAB | 2 h | 50 |
| 16 | 4 | 5 | 1 (4): 1.5 (5) | QSonica Q700, Amplitude 60%, pulse mode 5:1 | 50–60 | DMF, K2CO3, TBAB | 10 min | 70 (93% purity) |
| 17 | 4 | 5 | 1 (4): 1.5 (5) | QSonica Q700, Amplitude 60%, pulse mode 5:1 | 35–40 | CH3CN, K2CO3, TBAB | 10 min | 90 (100% purity) |
| 18 | 4 | 5 | 1 (4): 1.5 (5) | QSonica Q700, Amplitude 60%, pulse mode 5:1 | 45–50 | H2O, K2CO3, TBAB | 10 min | 12 (91% purity) |
| 19 | 4 | 5 | 1 (4): 3 (5) | QSonica Q700, Amplitude 60%, pulse mode 5:1 | 50–60 | CH3CN, K2CO3, TBAB | 10 min | 25 (91% purity) |
| 20 | 4 | 5 | 1 (4): 3 (5) | QSonica Q700, Amplitude 60%, pulse mode 5:1 | 50–60 | CH3CN, NaOH, TBAB | 10 min | 25 (91% purity) |
a
Reactions with reduced amount of solvent.