Ammonia → HCID 20351889, compound

HRID 371867Notes

Reaction equation

HRID 371867 reaction equation
[NH:1]([C:5]1[CH:16]=[CH:15][C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][C:6]=1[CH2:7][N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])C(C)=O.[ClH:22].N>C(O)C>[ClH:22].[NH2:1][C:5]1[CH:16]=[CH:15][C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][C:6]=1[CH2:7][N:8]([CH2:9][CH3:10])[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 20351843HCID 20351843, compound

Product 1

HCID 20351889HCID 20351889, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

19 gm of 2-acetamino-5-carbethoxy-N,N-diethyl-benzylamine were dissolved in 100 ml of ethanol, and after addition of 60 ml of concentrated hydrochloric acid the mixture was refluxed for 1 hour. Thereafter the mixture was poured over ice, made alkaline with ammonia and extracted three times with chloroform. The combined chloroform extracts were dried over sodium sulfate and evaporated in vacuo, and the residue was purified by chromatography on silicagel (elution agent: ethyl acetate); by addition of isopropanolic hydrochloric acid, 2-amino-5-carbethoxy-N,N-diethyl-benzylamine hydrochloride was obtained, which was recrystallized from ethanol and then had a melting point of 138-142° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. additionThereafter the mixture was poured over ice
  3. extractionextracted three times with chloroform
  4. dry with materialThe combined chloroform extracts were dried over sodium sulfate
  5. customevaporated in vacuo
  6. customthe residue was purified by chromatography on silicagel (elution agent: ethyl acetate)
  7. additionby addition of isopropanolic hydrochloric acid

Sources & evidence

ORD record
ord-c88baff2e965465a93658a97a4cdf879
Source dataset
uspto-grants-1978_05
Patent number
USRE029628

Reaction notes

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