Acetyl chloride → HCID 20534927, compound

HRID 1156559Notes

Reaction equation

HRID 1156559 reaction equation
C(N)CCCCCC.[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][C:21](Cl)=O)=[CH:14][CH:13]=1)([O-:11])=[O:10].[CH2:24]([NH:31][C:32](=[O:45])[CH2:33]CCC1C=CC([N+]([O-])=O)=CC=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].B#B.C(NCCCCC1C=CC([N+]([O-])=O)=CC=1)CCCCCC.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)(=O)C>CC(C)=O.O>[C:32]([N:31]([CH2:21][CH2:20][CH2:19][CH2:18][C:15]1[CH:14]=[CH:13][C:12]([N+:9]([O-:11])=[O:10])=[CH:17][CH:16]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])(=[O:45])[CH3:33]

Participants

10

Reactant 7

HCID 6367Acetyl chlorideHCID 81271-HeptanamineHCID 10340Sodium CarbonateHCID 797124-(4-Nitrophenyl)butyryl chlorideHCID 6328200DiboronHCID 12923060HCID 12923060, compoundHCID 54477910HCID 54477910, compound

Product 1

HCID 20534927HCID 20534927, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

n-Heptylamine was reacted with 4-(4-nitrophenyl)butanoyl chloride to provide 29.3 g. of N-n-heptyl-4-(4-nitrophenyl)butyramide. The amide was reacted with diborane to afford 25.8 g. of N-n-heptyl-4-(4-nitrophenyl)butylamine. The amine was dissolved in 70 ml. of acetone and added in one portion to 70 ml. of water containing 18.5 g. of sodium carbonate. The aqueous reaction mixture was stirred while 14.4 ml. of acetyl chloride in 70 ml. of acetone was added dropwise over one hour. The reaction mixture was stirred at room temperature for sixteen hours following the addition, and then the mixture was concentrated by evaporation of the acetone solvent under reduced pressure. The aqueous layer was extracted with diethyl ether, and the ethereal extract was then washed with water, with 2 N hydrochloric acid, again with water, and finally with saturated sodium chloride solution. The solution was dried and the solvent was removed by evaporation under reduced pressure to give 28.78 g of N-acetyl-N-n-heptyl-4-(4-nitrophenyl)butylamine.

Workup

  1. customto provide 29.3 g
  2. customto afford 25.8 g
  3. stirringThe reaction mixture was stirred at room temperature for sixteen hours
  4. additionthe addition
  5. concentrationthe mixture was concentrated by evaporation of the acetone solvent under reduced pressure
  6. extractionThe aqueous layer was extracted with diethyl ether
  7. extractionthe ethereal extract
  8. washwas then washed with water, with 2 N hydrochloric acid, again with water
  9. customThe solution was dried
  10. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-83936651861f46df889a436cb781d87a
Source dataset
uspto-grants-1982_06
Patent number
US04336269

Reaction notes

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