Potassium Hydroxide → HCID 23150774, compound

HRID 908900Notes

Reaction equation

HRID 908900 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][CH2:17][OH:18])=[CH:11][C:10]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl.Cl[CH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[CH2:17][O:18][CH2:25][CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:11][C:10]=1[O:19][CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 54535409HCID 54535409, compound

Product 1

HCID 23150774HCID 23150774, compoundYield 84.3%

Procedure

Following the procedure described in example 2, but starting from 3-(4-benzyloxy-3-methoxyphenyl)prop-2-en-1-ol (600 mg), potassium hydroxide (308 mg 85% wt) and 1-(3-chloropropyl)piperidine, hydrochloride (440 mg) in dimethylsufoxide (5 mL) affords 740 mg of trans-1-{3-[3-(4-benzyloxy-3-methoxyphenyl)-allyloxy]-propyl}piperidine containing 28% wt/wt DMSO used without any further purification. 3-(4-benzyloxy-3-methoxyphenyl)prop-2-en-1-ol can be prepared according to S. V. Reddy et al Chem. Lett. 32(11) 1038-9 (2003) or W. Gu et al Tetrahedron Lett. 41(32) 6079-82 (2000).

Sources & evidence

ORD record
ord-c71fb614340341b09c7899ad05bf2148
Source dataset
uspto-grants-2011_09
Patent number
US08017646B2

Reaction notes

Loading…