4-Phenylpiperidin-4-ol → HCID 18982827, compound

HRID 1464605Notes

Reaction equation

HRID 1464605 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:8]2[NH:9][C:10](=[O:12])[O:11][C:7]=2[CH:6]=1)=[O:4].[OH:15][C:16]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>>[OH:15][C:16]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:21][CH2:20][N:19]([CH2:2][CH:3]([C:5]2[CH:14]=[CH:13][C:8]3[NH:9][C:10](=[O:12])[O:11][C:7]=3[CH:6]=2)[OH:4])[CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 963874-Phenylpiperidin-4-olHCID 19889812(3H)-Benzoxazolone, 6-(chloroacetyl)-

Product 1

HCID 18982827HCID 18982827, compoundYield 25%

Procedure

By the procedures of Examples 8 and 2, 6-(2-chloroacetyl)-2(1H)-benzoxazolone and 4-hydroxy-4-phenylpiperidine were converted to present title product in 25% yield after recrystallization from ethanol/ether; m.p. 175°-177° C. NMR (methanol-d4) 7.51 (dd, J=1.5, 8.5 Hz, 2H), 7.35-7.29 (m, 3H), 7.24-7.19 (m, 2H), 7.05 (d, J=8 Hz, 1H), 4.94-4.90 (m, 1H--becomes dd J=3, 8.5 Hz with D2O wash), 2.96-2.90 (m, 2H), 2.80-2.57 (m, 4H), 2.19 (dq, J=4.5, 13 Hz, 2H), 1.74 (br d, J=14.5 Hz, 2H). IR(KBr) 3320, 3115, 2920, 2830, 1785, 1750.

Sources & evidence

ORD record
ord-71da7016a1634daab4eb7863272a35a9
Source dataset
uspto-grants-1994_04
Patent number
US05306723

Reaction notes

Loading…