1-Methylpiperazine → Hydrochloric Acid

HRID 1796499Notes

Reaction equation

HRID 1796499 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([Cl:17])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[CH:21][CH:20]=2)[CH2:3][CH2:2]1.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>C(Cl)Cl.C(OCC)C>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([N:32]4[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]4)(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[CH:21][CH:20]=2)[CH2:3][CH2:2]1.[ClH:17]

Participants

6

Reactant 2

HCID 531671-MethylpiperazineHCID 22181266HCID 22181266, compound

Product 2

HCID 313Hydrochloric AcidHCID 22181393HCID 22181393, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Following general procedure 36B: Used 1-(cyclopropylmethyl)-2-(4-ethoxybenzyl)-1H-benzimidazole-5-sulfonyl chloride (from 0.2 mmol of aniline precursor), 1-methylpiperazine (0.4 mmol) pyridine (0.5 mL) in CH2Cl2 (4 mL). The resulting mixture was stirred at room temperature overnight. Isolated the desired product as the HCl salt after column chromatography and treatment with 1 M HCl solution in diethyl ether (59 mg, 75%). 1H NMR (400 MHz, CD3OD): δ 8.02 (s, 1H), 7.71 (d, J=8.6 Hz, 1H), 7.64 (d, J=8.6 Hz, 1H), 7.13 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.8 Hz, 2H), 4.80 (s, 3H), 4.31 (s, 2H), 4.10 (d, J=7.2 Hz, 2H), 3.95 (q, J=8.0 Hz, 2H), 3.04–2.96 (m, 4H), 2.50–2.44 (m, 4H), 1.32 (t, J=8.0 Hz, 3H), 1.08–0.98 (m, 1H), 0.47–0.43 (m, 2H), 0.31–0.26 (m, 2H). MS (ESI) (M+1)+: 469. Anal. Calcd for C25H32N4O3S.2.7HCl.0.4H2O: C, 52.29; H, 6.23; N, 9.76. Found: C, 52.54; H, 6.21; N. 8.67.

Sources & evidence

ORD record
ord-f75fc23444924fa9844360865c714afd
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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