Phenylacetyl chloride → HCID 86670941, compound
Reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[C:32]1([CH2:38][C:39](Cl)=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N(CC)CC)C>ClCCl>[F:24][C:21]([F:22])([F:23])[C:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:10]2[CH2:9][CH2:8][CH:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:39](=[O:40])[CH2:38][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:31][CH:30]=3)[CH2:12][CH2:11]2)=[CH:15][CH:16]=1)([OH:29])[C:25]([F:28])([F:26])[F:27]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-(4-((4-(4-Aminobenzyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.336 mmol, 150 mg) and 2-phenylacetyl chloride (0.504 mmol, 0.067 mL, 78 mg) were combined in dichloromethane (3 mL) and cooled to 0° C. Triethylamine (0.672 mmol, 0.093 mL, 68.0 mg) was added and the mixture allowed to stir at 0° C. for 2 hours before allowing to warm to room temperature and stirring overnight. The reaction was diluted with dichloromethane and washed with water. The mixture was filtered through a hydrophobic frit and concentrated under vacuum. The residue was purified by flash chromatography on silica gel (eluent: dichloromethane-10% methanol/dichloromethane gradient) to afford the title compound (124.4 mg).
Workup
- temperatureto warm to room temperature
- stirringstirring overnight
- washwashed with water
- filtrationThe mixture was filtered through a hydrophobic frit
- concentrationconcentrated under vacuum
- customThe residue was purified by flash chromatography on silica gel (eluent: dichloromethane-10% methanol/dichloromethane gradient)
Sources & evidence
- ORD record
- ord-69b22f135c90436da21ffe6136e7e56b
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108939B2
Reaction notes
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