Ammonia → HCID 20351839, compound

HRID 1605592Notes

Reaction equation

HRID 1605592 reaction equation
[NH:1]([C:5]1[CH:19]=[CH:18][C:17]([C:20]([O:22]CC)=[O:21])=[CH:16][C:6]=1[CH2:7][N:8]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH3:9])C(C)=O.C(O)C.Cl.N>O>[NH2:1][C:5]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][C:6]=1[CH2:7][N:8]([CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[CH3:9]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 702EthanolHCID 20351881HCID 20351881, compound

Product 1

HCID 20351839HCID 20351839, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 21 gm of 2-acetamino-5-carbethoxy-N-cyclohexyl-N-methyl-benzylamine, 100 ml of ethanol, 90 ml of water and 60 ml of concentrated hydrochloric acid was refluxed for 1 hour. Thereafter, the reaction solution was cooled, poured over ice, made alkaline with ammonia and extracted three times with chloroform. The aqueous alkaline phase was evaporated to dryness in vacuo, the residue was thoroughly stirred with ethanol, and the mixture was filtered. The filtrate was evaporated to dryness in vacuo, and the residue was recrystallized from ethanol, yielding 2-amino-5-carboxy-N-cyclohexyl-N-methyl-benzylamine, m.p. 200°-205°C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureThereafter, the reaction solution was cooled
  3. additionpoured over ice
  4. extractionextracted three times with chloroform
  5. customThe aqueous alkaline phase was evaporated to dryness in vacuo
  6. filtrationthe mixture was filtered
  7. customThe filtrate was evaporated to dryness in vacuo
  8. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-b5f773e8c63f4ec7abb52420df08f58d
Source dataset
uspto-grants-1976_04
Patent number
US03950393

Reaction notes

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