Hydrochloric Acid → 2-cyclopentyl-1-[p-(N,N-dimethyl-2-aminoethoxy)phenyl]-1-(p-hydroxyphenyl)-1-butanol

HRID 637378

Reaction equation

HRID 637378 reaction equation
[CH:1]1([CH:6]([CH2:16][CH3:17])[C:7]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][N:19]([CH3:30])[CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26](Br)=[CH:25][CH:24]=1.Cl>C(O)C>[CH:1]1([CH:6]([CH2:16][CH3:17])[C:7]([C:26]2[CH:27]=[CH:28][C:23]([O:22][CH2:21][CH2:20][N:19]([CH3:30])[CH3:18])=[CH:24][CH:25]=2)([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[OH:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 213877(2-(4-Bromophenoxy)ethyl)dimethylamineHCID 13175265alpha-Cyclopentyl-p-hydroxybutyrophenone

Product 1

HCID 202569382-cyclopentyl-1-[p-(N,N-dimethyl-2-aminoethoxy)phenyl]-1-(p-hydroxyphenyl)-1-butanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-cyclopentyl-1-[p-(N,N-dimethyl-2-aminoethoxy)phenyl]-1-(p-hydroxyphenyl)-1-butanol, which was prepared from α-cyclopentyl-p-hydroxybutyrophenone and p-(N,N-dimethyl-2-aminoethoxy) bromobenzene according to the procedure of example 3, was dehydrated in ethanol in the presence of hydrochloric acid. The product was recrystallized from n-hexane, mp. 112°-120° C. and was found to be an 1:1 mixture of E- and Z-isomers.

Workup

  1. customThe product was recrystallized from n-hexane, mp. 112°-120° C.
  2. additionan 1:1 mixture of E- and Z-isomers

Sources & evidence

ORD record
ord-4fcd5461932b4ca9abf4342ca40471a3
Source dataset
uspto-grants-1985_12
Patent number
US04556677

Linked notes

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