Triethylamine → HCID 178453595, compound

HRID 1978358Notes

Reaction equation

HRID 1978358 reaction equation
Br[CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5][CH2:4]1.[C:18]1([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>C(O)C.O>[C:14]([O:13][C:11]([NH:10][CH2:9][C@H:6]1[CH2:7][CH2:8][C@H:3]([CH2:2][N:27]2[CH2:28][CH2:29][CH:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:25][CH2:26]2)[CH2:4][CH2:5]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 698734-PhenylpiperidineHCID 178453591HCID 178453591, compound

Product 1

HCID 178453595HCID 178453595, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2.51 g (8.20 mM) of N-(trans-4-bromomethyl-1-cyclohexylmethyl)-N-(tert-butoxycarbonyl)amine, 1.32 g (8.19 mM) of 4-phenylpiperidine, and 2.3 ml (16.5 mM) of triethylamine in ethanol (10 ml) was refluxed under nitrogen for 64 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. This crude product was purified by column chromatography (methanol-ethyl acetate: 10%) to provide the title compound as light-yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over MgSO4
  4. customThis crude product was purified by column chromatography (methanol-ethyl acetate: 10%)

Sources & evidence

ORD record
ord-27d73e3ce7114ceb97314c6aa116584d
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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