Ether hydrochloride → 1-(4-Chlorobenzyl)pyrrolidin-3-amine dihydrochloride

HRID 133551Notes

Reaction equation

C(OC([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:10]1)=O)(C)(C)C.[ClH:22].CCOCC>CO>[ClH:21].[ClH:22].[NH2:8][CH:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:10]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a methanol solution (80 mL) of the 3-[(tert-butoxycarbonyl)amino]-1-(4-chlorobenzyl)pyrrolidine (6.38 g, 20.5 mmol), was added 1 M HCl-Et2O (100 mL). The resulting mixture was stirred at 25° C. for 15 hours. The solvent was removed under reduced pressure to provide a solid, which was purified by recrystallization (methanol/acetonitrile=1:2, 130 mL) to thereby afford 3-amino-1-(4-chlorobenzyl)pyrrolidine dihydrochloride (4.939 g, 85%) as a white powder. 1H NMR (d6-DMSO, 300 MHz) δ 3.15 (br, 1H), 3.3-3.75 (br-m, 4H), 3.9 (br, 1H), 4.05 (br, 1H), 4.44 (br, 1H), 4.54 (br, 1H), 7.5-7.7 (m, 4H), 8.45 (br, 1H), 8.60 (br, 1H); the purity was determined by RPLC/MS (>99%). ESI/MS m/e 211.0 (M++H, C11H16ClN2).

Workup

customThe solvent was removed under reduced pressure
customto provide a solid, which
customwas purified by recrystallization (methanol/acetonitrile=1:2, 130 mL) to thereby afford 3-amino-1-(4-chlorobenzyl)pyrrolidine dihydrochloride (4.939 g, 85%) as a white powder

Sources & evidence

ORD record: ord-92504968f61742b891dceb0ee628d940
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390830B1

Reaction notes

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