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

HRID 654143Notes

Reaction equation

HRID 654143 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 6 M 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-4c5c417a03dc4188a8a714359f80e5af
Source dataset
uspto-grants-1992_07
Patent number
US05130330

Reaction notes

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