Cyclohexanemethylamine → HCID 57121373, compound

HRID 441595Notes

Reaction equation

HRID 441595 reaction equation
[CH:1]1([CH2:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>[OH-].[Na+].C1C=CC=CC=1>[C:15]([O:14][C:12](=[O:13])[CH2:11][CH2:10][NH:8][CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 76688CyclohexanemethylamineHCID 523716tert-butyl 3-chloropropanoate

Product 1

HCID 57121373HCID 57121373, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To 33.76 g of cyclohexylmethylamine was added with stirring 15.96 g of tert-butyl β -chloropropionate over a period of 30 minutes, while maintaining the temperature at 30°-70° C. The reaction mixture was held at 70° C. for an additional one hour. At the end of this period, the reaction mixture was taken up in 40 ml of 2N NaOH solution and 50 ml of benzene, transferred into a separatory funnel and well shaken. The benzene solution was separated, washed with water, dried over anhydrous sodium sulfate and filtered. After evaporation of benzene, the residue was distilled under reduced pressure to give 21.0 g (89 percent) of N-cyclohexylmethyl- β -alanine tert-butyl ester, B.P. 156° C./15 mmHg.

Workup

  1. temperaturewhile maintaining the temperature at 30°-70° C
  2. customThe benzene solution was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customAfter evaporation of benzene
  7. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-f023a2a055a34fbba8a14da70c47e2be
Source dataset
uspto-grants-1977_08
Patent number
US04041156

Reaction notes

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