Hydrochloric Acid → 1-[1-(3',4'-Dichloro-1,1'-biphenyl-3-yl)-2-piperazin-1-ylethyl]cyclohexanol dihydrochloride

HRID 1987412Notes

Reaction equation

HRID 1987412 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([C:30]3([OH:36])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[CH2:16][N:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[ClH:37].CO>C(OCC)C>[ClH:1].[ClH:37].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([C:30]3([OH:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)[CH2:16][N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 68854690Tert-butyl 4-[2-(3',4'-dichloro-biphenyl-3-yl)-2-(1-hydroxycyclohexyl)ethyl]piperazine-1-carboxylate

Product 1

HCID 166603391-[1-(3',4'-Dichloro-1,1'-biphenyl-3-yl)-2-piperazin-1-ylethyl]cyclohexanol dihydrochlorideYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

tert-butyl 4-[2-(3′,4′-dichloro-biphenyl-3-yl)-2-(1-hydroxycyclohexyl)ethyl]piperazine-1-carboxylate (0.39 g 0.73 mmol) was dissolved in diethyl ether (15 mL) then a 2N ethereal solution of hydrochloric acid (10 mL) was added. Methanol (approximately 1 mL) was then added until the resulting precipitate dissolved, and the homogeneous solution was stirred for 18 h. The precipitated product was collected by filtration, washed with diethyl ether and dried in a vacuum oven at 50° C. to yield 0.28 g (81%) of 1-[1-(3′,4′-dichloro-1,1′-biphenyl-3-yl)-2-piperazin-1-ylethyl]cyclohexanol dihydrochloride as a white solid. MS (ESI) m/z 433/435/437 ([M+H]+); HRMS: calcd for C24H30N2OCl2.2.00 HCl, 433.1813. found (ESI), 433.1813.

Workup

  1. dissolutiondissolved
  2. filtrationThe precipitated product was collected by filtration
  3. washwashed with diethyl ether
  4. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-22f89462f10e4cb185bf0ceca1e74c5a
Source dataset
uspto-grants-2009_06
Patent number
US07550485B2

Reaction notes

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