Triphenylphosphine dibromide → 4-[N-(7-Bromo-3-oxahept-1-yl)-N-(isopropyl)amino]-1-benzylpiperidine

HRID 1662118Notes

Reaction equation

HRID 1662118 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][N:9]([CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1)[CH:10]([CH3:12])[CH3:11].[Br:26]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCl>[Br:26][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][N:9]([CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1)[CH:10]([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 70579Triphenylphosphine dibromideHCID 674300054-[N-(7-Hydroxy-3-oxahept-1-yl)-N-(isopropyl)amino]-1-benzylpiperidine

Product 1

HCID 674285364-[N-(7-Bromo-3-oxahept-1-yl)-N-(isopropyl)amino]-1-benzylpiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[N-(7-Hydroxy-3-oxahept-1-yl)-N-(isopropyl)amino]-1-benzylpiperidine (3.7 g, 10.6 mmol) was treated with dibromotriphenylphosphorane (11.2 g, 26.6 mmol) in dichloromethane for 2 h. The reaction mixture was then was washed with 1 N sodium hydroxide, saturated sodium bicarbonate, brine, dried over magnesium sulfate and concentrated to give the title intermediate, which was used without further purification.

Workup

  1. washThe reaction mixture was then was washed with 1 N sodium hydroxide, saturated sodium bicarbonate, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7f4c38e7591c4a9889c724e3a20e6113
Source dataset
uspto-grants-2011_10
Patent number
US08030502B2

Reaction notes

Loading…