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Dimethylformamide → (+)-[2-(3,4-Dichloro-phenyl)-ethyl]-methyl-(2-pyrrolidin-1-yl-cyclohexyl)-amine

HRID 1598790
Notes
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Reaction equation

HRID 1598790 reaction equation
[N:1]1([C@H:6]2[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]2[NH:12][CH3:13])[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C)C=O.CS(O[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=1)(=O)=O>O>[Cl:33][C:28]1[CH:27]=[C:26]([CH2:25][CH2:24][N:12]([C@@H:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C@@H:6]2[N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH3:13])[CH:31]=[CH:30][C:29]=1[Cl:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 13377466cis-N-methyl-2-(1-pyrrolidinyl)cyclohexylamineHCID 147714762-(3,4-Dichlorophenyl)ethyl methanesulfonate

Product 1

HCID 10369311(+)-[2-(3,4-Dichloro-phenyl)-ethyl]-methyl-(2-pyrrolidin-1-yl-cyclohexyl)-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

(±)-cis-2-Pyrrolidinyl-N-methylcyclohexylamine (3 gm) was combined with anhydrous dimethylformamide (70 ml) and warmed to 60° C. 2-(3,4-dichlorophenyl)ethyl methanesulfonate (14 gm) was added to the warm amine solution over 3 days. The reaction mixture was diluted to 500 ml with water and extracted with chloroform. The combined extracts were washed with water and treated with a solution of hydrogen bromide in methanol. The solution was concentrated on a rotary evaporator and the residual dimethylformamide removed by distillation under high vacuum. The residue was triturated with 2-propanol to provide a white solid. The solid was recrystallized from 2-propanol. Analytical data are reported in Table I.

Workup

  1. extractionextracted with chloroform
  2. washThe combined extracts were washed with water
  3. additiontreated with a solution of hydrogen bromide in methanol
  4. concentrationThe solution was concentrated on a rotary evaporator
  5. customthe residual dimethylformamide removed by distillation under high vacuum
  6. customThe residue was triturated with 2-propanol
  7. customto provide a white solid
  8. customThe solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-182729f1462147579f8dddf0c91e8850
Source dataset
uspto-grants-1998_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05739158

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes