Hydrochloric Acid → HCID 10221322, compound

HRID 1250697Notes

Reaction equation

C(OC([NH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=2[C:20]#[N:21])[CH2:14][CH2:13]1)=O)(C)(C)C.[ClH:26]>C(OCC)(=O)C>[ClH:26].[NH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([C:18]2[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=2[C:20]#[N:21])[CH2:16][CH2:17]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-[1-(3-tert-butoxycarbonylamino-propyl)piperidin-4-yl] benzonitrile (0.73 g, 2.1 mmol) in ethyl acetate (100 ml), cooled to 0° C. was added hydrogen chloride gas, bubbled vigorously for 5 minutes. The reaction mixture was stirred for 10 minutes at 0° C., purged with argon and concentrated. Flushing with ethyl acetate×2 and concentration gave 2-[1-(3-arninopropyl)-piperidin4-yl] benzonitrile hydrochloride; 1H NMR (DMSO) d 2.00 (m, 2H), 2.10 (m, 2H), 2.28 (m, 2H), 2.95 (m, 2H), 3.18 (m, 4H), 3.56 (bd, 2H, J=11.7 Hz), 7.47 (m, 2H), 7.75 (bt, 1H, J=8 Hz), 7.84 (bd, 1H, J=7.9 Hz), 8.14 (bs, 2H), 11.1 (bd, 1H).

Workup

custombubbled vigorously for 5 minutes
custompurged with argon
concentrationconcentrated
customFlushing with ethyl acetate×2 and concentration

Sources & evidence

ORD record: ord-75dc190341344d4a89d103e72c423725
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06339090B1

Reaction notes

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