Hydrochloric Acid → HCID 20227972, compound

HRID 1731577Notes

Reaction equation

HRID 1731577 reaction equation
[CH:1]1([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15](=O)[CH3:16])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:18][CH:19]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[CH2:20][NH2:21].CO.[ClH:31]>ClCCl.C(OCC)C>[CH:1]1([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([NH:21][CH2:20][CH:19]([OH:18])[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[CH3:16])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:31].[CH:1]1([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([NH:21][CH2:20][CH:19]([OH:18])[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[CH3:16])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 20227975HCID 20227975, compound

Product 2

HCID 20227972HCID 20227972, compoundHCID 20227973HCID 20227973, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

N-[2-(4-cyclohexyloxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine was prepared from 1-(4-cyclohexyloxyphenyl)propan-2-one (2.5 g) and 2-hydroxy-2-(3-chlorophenyl)ethanamine (2.1 g) by an analogous procedure to that described in Example 1. After chromatography on silica gel eluting with 1% methanol in dichloromethane the purified amine was dissolved in diethyl ether, cooled and hydrogen chloride passed through the solution. Evaporation of the solvent and recrystallisation of the crude hydrochloride gave N-[2-(4-cyclohexyloxyphenyl)-1methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine hydrochloride m.p. 164°-166° C. (ethyl acetate-hexane) as a 48:52 mixture of diastereoisomers.

Workup

  1. temperaturecooled
  2. customEvaporation of the solvent and recrystallisation of the crude hydrochloride

Sources & evidence

ORD record
ord-293e73d7e60f454d87ded216e4c30147
Source dataset
uspto-grants-1986_11
Patent number
US04622342

Reaction notes

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