Isopropanol hydrochloride → 4-Aminomethyl-4-hydroxy-1-(6-oxo-6-phenylhexyl)piperidine dihydrochloride

HRID 344273Notes

Reaction equation

[OH:1][C:2]1([CH2:21][NH:22]C(OC(C)(C)C)=O)[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:4][CH2:3]1.[ClH:30].C(O)(C)C>C(O)(C)C>[ClH:30].[ClH:30].[NH2:22][CH2:21][C:2]1([OH:1])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

1H-NMR (CDCl3,ppm) δ: 1.36-1.82(20 H,m), 2.36-2.88(4 H,m), 2.60-2.67(2 H,m), 2.97(2 H,t,J=7.3 Hz), 3.14(2 H,d,J=6.6 Hz), 5.01(1 H,br), 7.42-7.59(3 H,m), 7.93-7.97(2 H,m) (2) 4-Hydroxy-1-(6-oxo-6-phenylhexyl)-4-tert-butoxycarbonylaminomethylpiperidine (3.6 g) was dissolved in isopropyl alcohol (30 ml) and 15% hydrochloric acid-isopropyl alcohol (10 ml) was added under ice-cooling, which was followed by stirring at 60° C. for 3 hr. The solvent was evaporated under reduced pressure to give 2.92 g of 4-aminomethyl-4-hydroxy-1-(6-oxo-6-phenylhexyl)piperidine dihydrochloride.

Workup

temperaturecooling
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-7d73a685631840f78dc4b5a2b2c74014
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05864039

Reaction notes

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