Water → N1-(4-Chlorophenyl)-N2-[[4-(1,1-dimethylethyl)phenyl]methyl]-N1-methyl-1,2-ethanediamine

HRID 855237Notes

Reaction equation

HRID 855237 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]([CH3:24])[CH2:21][CH2:22][NH2:23])=[CH:16][CH:15]=1.[BH4-].[Na+].O>CO>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:23][CH2:22][CH2:21][N:20]([C:17]2[CH:16]=[CH:15][C:14]([Cl:13])=[CH:19][CH:18]=2)[CH3:24])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 703244-tert-ButylbenzaldehydeHCID 88988N-(4-Chlorophenyl)-N-methylethylenediamineHCID 4311764Sodium borohydride

Product 1

HCID 68578813N1-(4-Chlorophenyl)-N2-[[4-(1,1-dimethylethyl)phenyl]methyl]-N1-methyl-1,2-ethanediamineYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.62 g (10 mmol) of 4-tert-butyl benzaldehyde and 1.85 g (10 mmol) of N-(4-chloro -phenyl)-N-methyl-ethane-1,2-diamine were dissolved in 20 ml methanol and the solution was stirred for 2 h at rt. 567 mg (15 mmol) of sodium borohydride were added in portions under nitrogen. The reaction mixture was stirred at rt over night. Water was added and the solvent was evaporated. The reaction mixture was extracted with diethyl ether and the organic layer was washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to leave the 2.97 g (90%) product as a yellow oil. 1H NMR (DMSO-d6, 300 MHz): δ 7.34 (d, 2H), 7.24 (d, 2H), 7.13 (d, 2H), 6.64 (d, 2H), 3.77 (s, 2H), 3.42 (t, 2H), 2.91 (s, 3H), 2.83 (t, 2H), 1.30 (s, 9H).

Workup

  1. stirringThe reaction mixture was stirred at rt over night
  2. customthe solvent was evaporated
  3. extractionThe reaction mixture was extracted with diethyl ether
  4. washthe organic layer was washed with saturated aqueous NaCl solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b018923e6f1a4f08a52df0d9566bfdb7
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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