Hydrochloric Acid → 3-(4-Piperidinyl)-1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-one hydrochloride

HRID 550385Notes

Reaction equation

HRID 550385 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:20][CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=3[NH:16][C:15]2=[O:25])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:26]>C(OCC)(=O)C>[ClH:26].[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH2:20][CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=3[NH:16][C:15]2=[O:25])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58823744Tert-butyl 4-(2-oxo-1,2,4,5-tetrahydrobenzo[d][1,3]diazepin-3-yl)piperidine-1-carboxylate

Product 1

HCID 671734603-(4-Piperidinyl)-1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-one hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(1-t-butoxycarbonyl-4-piperidinyl)-1,3,4,5-tetrahydro-2H-1,3-benzodiazapin-2-one (4.80 g, 13.9 mmol) in ethyl acetate (300 mL) was saturated with hydrogen chloride gas at 0° C. The reaction was allowed to warm to room temperature and stirred overnight. The solid was filtered and washed with ethyl acetate. The ethyl acetate filtrate was concentrated for a second crop. The title compound was obtained as a solid (2.94 g). MS: m/z=246 (M+1). 1H NMR (500 MHz, CD3OD) δ 7.10 (m, 2H), 6.94 (d, J=8 Hz, 1H), 6.91 (t, J=8 Hz, 1H), 4.35 (tt, J=10, 1 Hz, 1H), 3.52 (m, 4H), 3.12 (t, J=12 Hz, 2H), 3.05 (m, 2H), 2.07 (qd, J=12, 4 Hz, 2H), 1.99 (m, 2H).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with ethyl acetate
  3. concentrationThe ethyl acetate filtrate was concentrated for a second crop

Sources & evidence

ORD record
ord-b03d86123092479e97028db242d87d90
Source dataset
uspto-grants-2011_05
Patent number
US07947678B2

Reaction notes

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