1,1-Dichloroethane → HCID 18675485, compound

HRID 343629Notes

Reaction equation

C([O:5][NH:6][C:7]([CH:9]1[CH2:14][NH:13][CH2:12][CH2:11][N:10]1[S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)(=[O:17])=[O:16])=[O:8])(C)(C)C.[Cl:26]C(Cl)C>C(O)C>[ClH:26].[OH:5][NH:6][C:7]([CH:9]1[CH2:14][NH:13][CH2:12][CH2:11][N:10]1[S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)(=[O:17])=[O:16])=[O:8]

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of (+)-N-(t-butyloxy)-1-(4-methoxybenzenesulfonyl)-2-piperazinecarboxamide (30 mg, in dichloroethane is added ethanol (1 drop). The solution is cooled to -10° C. and hydrogen chloride gase is bubbled through for 5 minutes. The reaction is then sealed and stirred for 24 hours at which time the volume is reduced to 1/3 by evaporation and the precipitated solids are filtered and dried (in vacuo) to give (+)-N-hydroxy-1-(4-methoxybenzenesulfonyl)-2-piperazinecarboxamide hydrochloride as a white solid. Melting point 167° C. (dec.). Mass spectrum (thermospray): m/Z 343 (m+1 100%). 1H NMR (CD3OD, 250 MHz, ppm): δ7.76 (d, J=8.9 Hz, 2 H), 7.07 (d, J=8.9 Hz, 2 H), 3.87 (bs, H2O ), 4.19 (d, J=3.3 Hz, 1 H), 3.87 (s, 3 H), 3.58 (bd, J=6.2 Hz, 1 H), 3.42 (bd, J=6.1 Hz, 1 H), 3.30 (bs, CD3OD), 3.16 (d, J=13.5 Hz, 1 H), 2.87 (bd, J=13.3 Hz, 1 H), 2.69 (dd, J=13.3, 3.0 Hz, 1 H), 2.51 (dt, J=12.5, 3.8 Hz, 1 H).

Workup

customhydrogen chloride gase is bubbled through for 5 minutes
customThe reaction is then sealed
customis reduced to 1/3 by evaporation
filtrationthe precipitated solids are filtered
customdried (in vacuo)

Sources & evidence

ORD record: ord-38bd7a07c0e6489c81c9eb782f5ef39c
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05861510

Reaction notes

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