Hydrochloric Acid → (2-Bromo-phenyl)-piperazin-1-yl-methanone hydrochloride

HRID 1665585Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Br:21])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:23]>>[ClH:23].[Br:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:14]([N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:22]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 17952334Tert-butyl 4-(2-bromobenzoyl)piperazine-1-carboxylate

Product 1

HCID 66625832(2-Bromo-phenyl)-piperazin-1-yl-methanone hydrochlorideYield 95%

Procedure

HCl (50 mL) was added to 4-(2-bromo-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester (9 g, 24.4 mmol) at 0° C. The resulting mixture was stirred for 4 hours, then concentrated. The resulting residue was washed with 1% MeOH in ethyl acetate and dried under reduced pressure to afford 7.1 g (95%) of (2-bromo-phenyl)-piperazin-1-yl-methanone hydrochloride salt, LCMS: 306.6 (M+1)+, 86.8%, 1H NMR: (DMSO-d6): δ 9.6 (s, 2H), 7.7 (d, 1H), 7.45 (m, 3H), 4.0 (m, 1H), 3.76 (m, 1H), 3.18 (bs, 2H), 3.06 (bs, 2H).

Workup

concentrationconcentrated
washThe resulting residue was washed with 1% MeOH in ethyl acetate
customdried under reduced pressure

Sources & evidence

ORD record: ord-91746ebd5bf747bdaee3119c1a5c5db1
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039463B2

Reaction notes

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