Triethylamine → 1-[4-Hydroxy-4-(3-(trifluoromethyl)phenyl)-1-piperidinyl]-2-(6-benzimidazolyl)-1-ethanone

HRID 456410

Reaction equation

HRID 456410 reaction equation
[NH:1]1[C:5]2[CH:6]=[C:7]([CH2:10][C:11]([OH:13])=O)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[OH:14][C:15]1([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O.C(OCC)(=O)C>[OH:14][C:15]1([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=2)[CH2:20][CH2:19][N:18]([C:11](=[O:13])[CH2:10][C:7]2[CH:8]=[CH:9][C:4]3[NH:3][CH:2]=[N:1][C:5]=3[CH:6]=2)[CH2:17][CH2:16]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 752554-[3-(Trifluoromethyl)phenyl]-4-piperidinolHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 30466112-(1H-Benzo[d]imidazol-6-yl)acetic acid

Product 1

HCID 1785201931-[4-Hydroxy-4-(3-(trifluoromethyl)phenyl)-1-piperidinyl]-2-(6-benzimidazolyl)-1-ethanone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.46 g (0.0083 mol) of 1H-benzimidazol-6-ylacetic acid from preparation 3, 2.0 g (0.0081 mol) of 4-hydroxy-4-(3-(trifluoromethyl)phenyl)piperidine, 3.6 g of BOP and 3.4 ml of triethylamine in 40 ml of dimethylformamide is stirred at ambient temperature overnight. A mixture of ethyl acetate and of water is added, the two phases are separated, the organic phase is dried over sodium sulfate and the solvent is evaporated. The crude product is purified by chromatography on a column of silica gel, elution being carried out with an ethyl acetate/methanol=9/1 mixture, and the title compound is thus obtained.

Workup

  1. customthe two phases are separated
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. customthe solvent is evaporated
  4. customThe crude product is purified by chromatography on a column of silica gel, elution

Sources & evidence

ORD record
ord-26c678bbe47845178a2d85dbbf176f86
Source dataset
uspto-grants-2007_03
Patent number
US07186720B2

Linked notes

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