Ammonia → cis-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine

HRID 1598789Notes

Reaction equation

HRID 1598789 reaction equation
[N:1]1([C@H:6]2[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]2[N:12](C(OC(C)(C)C)=O)[CH3:13])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.N>>[N:1]1([C@H:6]2[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]2[NH:12][CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 86745978(+/-)-cis-2-Pyrrolidinyl-N-t-butyloxycarbonyl-N-methylcyclohexylamine

Product 1

HCID 13377466cis-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine

Conditions

Temperature
60 °C

Procedure

(±)-cis-2-Pyrrolidinyl-N-t-butyloxycarbonyl-N-methylcyclohexylamine (247 gm) was slowly added to 6M hydrochloric acid at 60° C. with vigorous stirring. The solution was stirred an additional 5 minutes at 60° C. and poured onto ice (200 gm). Excess concentrated aqueous ammonia was added and the mixture was extracted with methylene chloride. The combined extracts were dried (Na2SO4) and the solvent removed on a rotary evaporator. The residue was distilled (78° C. at 0.3 mm Hg) to give the product as a colorless oil.

Workup

  1. additionpoured onto ice (200 gm)
  2. extractionthe mixture was extracted with methylene chloride
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customthe solvent removed on a rotary evaporator
  5. distillationThe residue was distilled (78° C. at 0.3 mm Hg)

Sources & evidence

ORD record
ord-049a10d333614782a47d81578727c7e7
Source dataset
uspto-grants-1998_04
Patent number
US05739158

Reaction notes

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