Potassium Carbonate → 2-Benzyloxy-5-(2-[Benzyl-6-(N-Methylanilino)-2-Hexylamino]-1-Hydroxyethyl)Benzamide

HRID 972069Notes

Reaction equation

HRID 972069 reaction equation
[CH2:1]([NH:8][CH:9]([CH3:22])[CH2:10][CH2:11][CH2:12][CH2:13][N:14]([CH3:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([O:30][C:31]1[CH:39]=[CH:38][C:37]([C:40](=[O:43])[CH2:41]Br)=[CH:36][C:32]=1[C:33]([NH2:35])=[O:34])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])([O-])=O.[K+].[K+].[BH4-].[Na+]>CN(C)C=O.O>[CH2:23]([O:30][C:31]1[CH:39]=[CH:38][C:37]([CH:40]([OH:43])[CH2:41][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][N:14]([CH3:21])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH3:22])=[CH:36][C:32]=1[C:33]([NH2:35])=[O:34])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 30183385-(Bromoacetyl)-2-(phenylmethoxy)benzamideHCID 4311764Sodium borohydrideHCID 20396467N-(5-benzylaminohexyl)-N-methylaniline

Product 1

HCID 536576542-Benzyloxy-5-(2-[Benzyl-6-(N-Methylanilino)-2-Hexylamino]-1-Hydroxyethyl)Benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To N-(5-benzylaminohexyl)-N-methylaniline (3.06 g= 10 mmol) and 3.48 g (10 mmol) 2-benzyloxy-5-(bromoacetyl)benzamide in 35 ml dimethylformamide, add 2.70 g (20 mmol) K2CO3. Stir 20 hrs. and pour into 150 ml water. Allow the gum to settle, decant, and dissolve the gum in ether. Extract with 1.0 N HCl, and then neutralize into NaHCO3 and extract with EtOAc. Dry, concentrate, and dissolve the oil in 50 ml ethanol. Add 0.3 g (8 mmol) NaBH4, stir 20 hrs., and concentrate. Partition between EtOAc and 1.0 N NaHCO3. Dry and concentrate to give a yellow foam.

Workup

  1. customdecant
  2. dissolutiondissolve the gum in ether
  3. extractionExtract with 1.0 N HCl
  4. extractionextract with EtOAc
  5. customDry
  6. concentrationconcentrate
  7. dissolutiondissolve the oil in 50 ml ethanol
  8. stirringstir 20 hrs
  9. concentration, and concentrate
  10. customPartition between EtOAc and 1.0 N NaHCO3
  11. customDry
  12. concentrationconcentrate
  13. customto give a yellow foam

Sources & evidence

ORD record
ord-3297302947d848b8b6c0000a894e700d
Source dataset
uspto-grants-1979_07
Patent number
US04163053

Reaction notes

Loading…