Hydrochloric Acid → cis-2-Pyrrolidin-1-yl-cyclohexylamine dihydrochloride

HRID 1950896

Reaction equation

HRID 1950896 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)(C)(C)C.[ClH:20]>O1CCOCC1>[ClH:20].[ClH:20].[N:14]1([C@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C@H:8]2[NH2:7])[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66680888cis-(2-Pyrrolidin-1-yl-cyclohexyl)-carbamic acid tert-butyl ester

Product 1

HCID 66680564cis-2-Pyrrolidin-1-yl-cyclohexylamine dihydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

cis-(2-Pyrrolidin-1-yl-cyclohexyl)-carbamic acid tert-butyl ester (1.8 g, 6.7 mmol) was dissolved in dioxane. 4H HCl in dioxane (17 mL, 67 mmol) were added and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated off. The residue was crystallized with ethanol and yielded cis-2-pyrrolidin-1-yl-cyclohexylamine dihydrochloride as a white solid (1.37 g, 85%), MS: m/e=169.2 [(M+H)+].

Workup

  1. customThe solvent was evaporated off
  2. customThe residue was crystallized with ethanol

Sources & evidence

ORD record
ord-826d66ca1440479b9ffe73346e50cb50
Source dataset
uspto-grants-2013_03
Patent number
US08404673B2

Linked notes

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