Triethylamine → 2-Bromo-1-[3-(4-phenyl-piperidin-1-yl)-pyrrolidin-1-yl]-ethanone

HRID 406484Notes

Reaction equation

HRID 406484 reaction equation
Cl.Cl.[C:3]1([CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:19][CH2:18][NH:17][CH2:16]3)[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCN(CC)CC.[Br:27][CH2:28][C:29](Br)=[O:30]>C1COCC1>[Br:27][CH2:28][C:29]([N:17]1[CH2:18][CH2:19][CH:15]([N:12]2[CH2:11][CH2:10][CH:9]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH2:14][CH2:13]2)[CH2:16]1)=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 688998884-Phenyl-1-pyrrolidin-3-yl-piperidine dihydrochloride

Product 1

HCID 597649822-Bromo-1-[3-(4-phenyl-piperidin-1-yl)-pyrrolidin-1-yl]-ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-phenyl-1-pyrrolidin-3-yl-piperidine dihydrochloride (prepared using general procedures E, F, 0.051 g, 0.17 mmol) and Et3N (0.05 mL, 0.34 mmol) in THF (1.7 mL) was added bromoacetylbromide (0.015 mL, 0.17 mmol). The reaction mixture was stirred at ambient temperature for about 12 h then concentrated in vacuo to give 2-bromo-1-[3-(4-phenyl-piperidin-1-yl)-pyrrolidin-1-yl]-ethanone that was used without further purification.

Workup

  1. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-7de86b4e5de4421e876008ed39cd2b93
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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