Piperidine → 2-(4-Fluorophenyl)-1-{4-[(2-piperidyl)ethoxy]benzoyl}-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

HRID 2114746Notes

Reaction equation

HRID 2114746 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:37]=[CH:36][C:8]([C:9]([CH:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:19]=3)[CH2:14][CH2:13][N:12]2[C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[O:10])=[CH:7][CH:6]=1.[NH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>CN(C)C=O>[F:35][C:32]1[CH:31]=[CH:30][C:29]([N:12]2[CH2:13][CH2:14][C:15]3[C:20](=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:16]=3)[CH:11]2[C:9](=[O:10])[C:8]2[CH:36]=[CH:37][C:5]([O:4][CH2:3][CH2:2][CH:39]3[CH2:40][CH2:41][CH2:42][CH2:43][NH:38]3)=[CH:6][CH:7]=2)=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 234408451-[4-(2-Bromethoxy)benzoyl]-2-(4-fluorophenyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 536534802-(4-Fluorophenyl)-1-{4-[(2-piperidyl)ethoxy]benzoyl}-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinolineYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[4-(2-bromethoxy)benzoyl]-2-(4-fluorophenyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline (0.80 g, 1.43 mmol) and piperidine (0.86 g, 10.1 mmol) in dimethylformamide was stirred at room temperature for 3 hours. The reaction was quenched with brine and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, concentrated, and purified by chromatography (SiO2, ethyl acetate and 3-5% methanol/ethyl acetate) to provide the title compound (0.594 g, 74% yield): 1H NMR (CDCl3) 8.00 (m, 2H), 7.40 (m, 4H), 6.79-6.92 (m, 10H), 5.87 (s, 1H), 5.02 (s, 2H), 4.15 (t, 2H), 3.72 (m, 1H), 3.48 (m, 1H), 3.07 (m, 1H), 2.79 (t and m, 3H), 2.51 (m, 4H), 1.61 (m, 4H), 1.46 (m, 2H); ES-MS (m/z) 565 [M+H]+.

Workup

  1. customThe reaction was quenched with brine
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by chromatography (SiO2, ethyl acetate and 3-5% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-ed76d369766a436f9bd0ce6713ead0f0
Source dataset
uspto-grants-2008_10
Patent number
US07435729B2

Reaction notes

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