Dimethylformamide → N-(4-tert-pentylbenzyl)-N-methyl-1-naphthylmethylamine hydrochloride

HRID 1741735Notes

Reaction equation

HRID 1741735 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O.[C:25]([C:30]1[CH:37]=[CH:36][C:33]([CH2:34][Cl:35])=[CH:32][CH:31]=1)([CH2:28][CH3:29])([CH3:27])[CH3:26]>O>[ClH:35].[C:25]([C:30]1[CH:37]=[CH:36][C:33]([CH2:34][N:2]([CH2:3][C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=[CH:6][CH:5]=2)[CH3:1])=[CH:32][CH:31]=1)([CH2:28][CH3:29])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 84474N-Methyl-N-naphthylmethylamineHCID 141400Toluene, alpha-chloro-p-(1,1-dimethyl-propyl)-

Product 1

HCID 18957493N-(4-tert-pentylbenzyl)-N-methyl-1-naphthylmethylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1.03 g of N-methyl-1-naphthylmethylamine, 0.7 g of sodium carbonate and 10 ml of dimethylformamide was added 1.3 g of 4-tert-pentylbenzyl chloride and was stirred at room temperature for 16 hours. The reaction mixture was poured into water and extracted with benzene, and the benzene solution was washed with water. After distilling away benzene, 1.5 ml of concentrated hydrochloric acid was added and then an excess of concentrated hydrochloric acid was removed. A small amount of acetone was added and 1.33 g of formed white crystal was filtrated. White crystal of N-(4-tert-pentylbenzyl)-N-methyl-1-naphthylmethylamine hydrochloride (Compound of Example 12) was obtained by recrystallization from acetone.

Workup

  1. extractionextracted with benzene
  2. washthe benzene solution was washed with water
  3. distillationAfter distilling away benzene, 1.5 ml of concentrated hydrochloric acid
  4. additionwas added
  5. customan excess of concentrated hydrochloric acid was removed
  6. additionA small amount of acetone was added
  7. filtration1.33 g of formed white crystal was filtrated

Sources & evidence

ORD record
ord-2df96ef726e9474bad41f2ba8af3e716
Source dataset
uspto-grants-1994_08
Patent number
US05334628

Reaction notes

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