Acetic Acid → 4-[3-(4-Hydroxy-4-phenyl-piperidin-1-yl)-propyl]-1-(3-trifluoromethyl-phenyl)-[1,4]diazepan-5-one

HRID 1096236Notes

Reaction equation

HRID 1096236 reaction equation
[O:1]=[C:2]1[N:8]([CH2:9][CH2:10][CH:11]=O)[CH2:7][CH2:6][N:5]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[CH2:4][CH2:3]1.[C:23]1([C:29]2([OH:35])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.B.N1C=CC=CC=1.CC(O)=O>ClCCCl.CCO>[OH:35][C:29]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:34][CH2:33][N:32]([CH2:11][CH2:10][CH2:9][N:8]2[C:2](=[O:1])[CH2:3][CH2:4][N:5]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[CH2:6][CH2:7]2)[CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 963874-Phenylpiperidin-4-olHCID 2723995Borane;pyridineHCID 866383883-[7-Oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-propionaldehyde

Product 1

HCID 591592464-[3-(4-Hydroxy-4-phenyl-piperidin-1-yl)-propyl]-1-(3-trifluoromethyl-phenyl)-[1,4]diazepan-5-oneYield 44%

Reagents, catalysts & solvents 1

HCID 229016121,2-Dichloroethane ethanolSolvent

Procedure

To a solution of 3-[7-oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-propionaldehyde 0.016 g (0.05 mmol) and 4-phenyl-piperidin-4-ol 0.018 g (0.10 mmol) in DCE/EtOH 1:1 (0.5 ml) was added pyridine-borane complex (25 μL of 8 M solution in pyridine, 0.2 mmol) and AcOH (25 μL, 0.4 mmol) and the mixture stirred for 16 h. The mixture was then evaporated to dryness and purified by preparative HPLC, affording the title compound 0.01 g (44%) as a white solid. MS: 476.2 (MH+).

Workup

  1. customThe mixture was then evaporated to dryness
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-08bf37eec1154abcab77aabfd51a5773
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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