Triethylamine → HCID 70629129, compound

HRID 616763Notes

Reaction equation

HRID 616763 reaction equation
C[CH:2](Cl)[C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])=[O:4].[CH2:22](N(CC)CC)C.Cl.[CH3:30][NH:31][C:32](=[O:37])[CH2:33][CH2:34][NH:35][CH3:36]>C1(C)C(C)=CC=CC=1.C(OCC)C>[ClH:20].[CH3:30][NH:31][C:32]([CH2:33][CH2:34][N:35]([CH3:36])[CH2:2][C:3]([N:5]([C:6]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])[CH3:22])=[O:4])=[O:37]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 25190939N,N~3~-Dimethyl-beta-alaninamide--hydrogen chloride (1/1)HCID 54271004HCID 54271004, compound

Product 1

HCID 70629129HCID 70629129, compoundYield 155.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7237O-XyleneSolvent

Procedure

A mixture of 16.1 g of 2-(methyl-chloroacetamido)-5-chlorobenzophenone, 10 g of triethylamine and 7.6 g of 3-methylaminopropionic acid methylamide hydrochloride in 500 ml of anhydrous xylene is heated to reflux for 12 hours whilst stirring. The triethylamine hydrochloride which has precipitated is filtered off with suction after cooling and, after extracting three times by shaking with water, the organic phase is dried over anhydrous potassium carbonate, filtered and evaporated in vacuo. The oily crude base thus obtained (18 g) is dissolved in 800 ml of anhydrous diethyl ether and filtered and 17.0 g of 2-(5-methylaminocarbonyl-N-methyl-3-methyl-3-aza-pentanamido)-5-chlorobenzophenone hydrochloride (77% of theory), with a melting point of 151°-153°, are obtained by passing dry hydrogen chloride into the solution.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 12 hours
  3. customThe triethylamine hydrochloride which has precipitated
  4. filtrationis filtered off with suction
  5. temperatureafter cooling
  6. extractionafter extracting three times
  7. stirringby shaking with water
  8. dry with materialthe organic phase is dried over anhydrous potassium carbonate
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe oily crude base thus obtained (18 g)
  12. filtrationfiltered

Sources & evidence

ORD record
ord-bd83244f89ce4795a04a52b00703d9cb
Source dataset
uspto-grants-1978_02
Patent number
US04075409

Reaction notes

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