Benzoic Acid → [4-(4-Chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl](phenyl)methanone
Reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]2[C:44]3[CH:45]=[CH:46][S:47][C:43]=3[CH2:42][CH2:41][NH:40]2)=[CH:35][CH:34]=1>ClCCl.CN(C)C=O.O>[Cl:32][C:33]1[CH:34]=[CH:35][C:36]([CH:39]2[C:44]3[CH:45]=[CH:46][S:47][C:43]=3[CH2:42][CH2:41][N:40]2[C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:9])=[CH:37][CH:38]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
Benzoic acid (46 mg, 0.38 mmol) and 1-hydroxybenzotriazole (55 mg, 0.41 mmol) were dissolved in a mixture of dichloromethane (1 mL) and N,N-dimethylformamide (0.5 mL). N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (79 mg, 0.41 mmol) was added and the mixture was shaken 0.5 hour at room temperature. 4-(4-Chlorophenyl)4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (100 mg, 0.38 mmol) dissolved in dichloromethane (0.5 ml) was added and the mixture was shaken at 1000 rpm for 3 hours. Water (1 mL) was added and the mixture was shaken at 1000 rpm overnight at room temperature. The organic phase was evaporated to give 129 mg (97%) of the title compound as an oil.
Workup
- additionwas added
- stirringthe mixture was shaken at 1000 rpm for 3 hours
- stirringthe mixture was shaken at 1000 rpm overnight at room temperature
- customThe organic phase was evaporated
Sources & evidence
- ORD record
- ord-a51afe83243148a18b38a83e7c8276ef
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06177443B1
Reaction notes
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