Acetic Acid → 1-dimethylamino-N-[3,4-dichlorotolyl]-cyclohexane carboxamide hydrochloride

HRID 2072020Notes

Reaction equation

HRID 2072020 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]1([C:9]([NH:11][C:12]2[C:17]([Cl:18])=[C:16]([Cl:19])[CH:15]=[CH:14][C:13]=2[CH3:20])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl.C(O)(=O)C.CCOCC>C(O)C>[ClH:18].[CH3:1][N:2]([CH3:21])[C:3]1([C:9]([NH:11][C:12]2[C:17]([Cl:18])=[C:16]([Cl:19])[CH:15]=[CH:14][C:13]=2[CH3:20])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 867338441-dimethylamino-N-[3,4-dichlorotolyl]-cyclohexane carboxamide

Product 1

HCID 867338451-dimethylamino-N-[3,4-dichlorotolyl]-cyclohexane carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Dimethylamino-N-[3,4-dichlorotolyl]-cyclohexane carboxamide (0.658 g.,) was dissolved in ethanol (5 ml.) and ethereal hydrogen chloride (10 ml.) was added. The solution was evaporated to leave a colourless oil which was taken up in the minimum volume of acetic acid. Dropwise addition of ether, with scratching and cooling, precipitated the hydrochloride as colourless prisms which was dried over potassium hydroxide in vacuo (0.688 g., m.p. 160°-170°). Recrystallisation from ethanol (addition of ether) afforded 1-dimethylamino-N-[3,4-dichlorotolyl]-cyclohexane carboxamide hydrochloride as white prisms (0.351 g., 48%); m.p. 162°-166° C.

Workup

  1. customThe solution was evaporated
  2. customto leave a colourless oil which
  3. temperaturecooling
  4. customprecipitated the hydrochloride as colourless prisms which
  5. dry with materialwas dried over potassium hydroxide in vacuo (0.688 g., m.p. 160°-170°)
  6. customRecrystallisation from ethanol (addition of ether)

Sources & evidence

ORD record
ord-94e5847119b94d099175b766cf476d27
Source dataset
uspto-grants-1977_09
Patent number
US04049663

Reaction notes

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