Benzaldehyde → HCID 20407066, compound

HRID 2418167Notes

Reaction equation

HRID 2418167 reaction equation
N[CH2:2][CH2:3][CH2:4][N:5]([CH3:7])[CH3:6].[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:16]([BH3-])#[N:17].[Na+].Cl>CO.C(O)(=O)C>[CH3:6][N:5]([CH2:4][CH2:3][CH2:2][N:17]([CH2:16][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:7]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 20407066HCID 20407066, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 10.22 g of 3-aminopropyldimethylamine in 100 ml of methanol was neutralized with 12 ml of glacial acetic acid and mixed with 100 g of benzaldehyde. To the stirred mixture, was added portionwise 8.38 g of sodium cyanoborohydride. The mixture was allowed to react at room temperature for 16 hours. The reaction mixture was adjusted to pH 1 with concentrated hydrochloric acid, and stripped of the methanol by distillation under reduced pressure. The residue was treated with 200 ml of water and 200 ml of chloroform. The aqueous layer was separated and extracted with 200 ml of chloroform to remove the benzaldehyde. The aqueous layer was adjusted to pH 12 with sodium hydroxide and extracted twice with 200 ml of chloroform. The chloroform extract was dried over sodium sulfate and freed from the solvent by distillation under reduced pressure to yield 26 g (92% yield) of [3-(N,N-dimethylamino)propyl]dibenzylamine.

Workup

  1. customto react at room temperature for 16 hours
  2. distillationstripped of the methanol by distillation under reduced pressure
  3. additionThe residue was treated with 200 ml of water and 200 ml of chloroform
  4. customThe aqueous layer was separated
  5. extractionextracted with 200 ml of chloroform
  6. customto remove the benzaldehyde
  7. extractionextracted twice with 200 ml of chloroform
  8. extractionThe chloroform extract
  9. dry with materialwas dried over sodium sulfate
  10. distillationfreed from the solvent by distillation under reduced pressure

Sources & evidence

ORD record
ord-984b98789d734240b2fa4fb5b8f9347b
Source dataset
uspto-grants-1984_09
Patent number
US04472304

Reaction notes

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