1-(3-Bromopropoxy)-3-chlorobenzene → Tert-butyl 4-{4-[3-(3-chlorophenoxy)propoxy]phenyl}-3-hydroxypiperidine-1-carboxylate

HRID 1176445Notes

Reaction equation

HRID 1176445 reaction equation
[OH:1][CH:2]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1.Br[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=1>>[Cl:33][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[O:26][CH2:25][CH2:24][CH2:23][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH:7]2[CH2:6][CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3][CH:2]2[OH:1])=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 27349291-(3-Bromopropoxy)-3-chlorobenzeneHCID 21713087(3S,4S)-tert-Butyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate

Product 1

HCID 68505679Tert-butyl 4-{4-[3-(3-chlorophenoxy)propoxy]phenyl}-3-hydroxypiperidine-1-carboxylate

Procedure

Analogously to Method I, 0.750 g of tert-butyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate and 0.832 g of 1-(3-bromopropoxy)-3-chlorobenzene are reacted. The title compound is obtained as a slightly yellowish oil. Rf=0.30 (1:2 EtOAc-heptane); Rt=5.55.

Sources & evidence

ORD record
ord-0b9302ee530c4f8f9d387929bd139c88
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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