Water → HCID 53759631, compound

HRID 850208Notes

Reaction equation

HRID 850208 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16]([C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C.O>C1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:1][N:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([C:16]([CH3:18])([CH3:17])[CH3:19])=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 74034-tert-Butylbenzoic acidHCID 8471TriethylamineHCID 193663851-([1,1'-Biphenyl]-2-yl)-N-methylmethanamine

Product 1

HCID 53759631HCID 53759631, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6212ChloroformSolvent

Procedure

Orthophenylbenzoic acid (10 g) and thionyl chloride (18.7 g) were mixed with 100 ml of chloroform, followed by heating for 4 hours under reflux. The reaction mixture was concentrated under reduced pressure, and the resulting concentrate was added dropwise to 40 ml of a 40% aqueous solution of methylamine under ice cooling. The temperature of the resulting mixture was allowed to rise to room temperature, at which a reaction was allowed to proceed under stirring for 4 days. 2 N hydrochloric acid was added to terminate the reaction, followed by the extraction of the resulting mixture with chloroform. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was collected, from which the solvent was distilled off so that N-methyl-2-phenylbenzoic acid amide was obtained. The acid amide was reduced with 0.54 g of lithium aluminum hydride in diethyl ether, whereby 1.46 g of N-methyl-2-phenylbenzylamine were obtained. The benzylamine was reacted with an acid chloride, which had been derived from 1.45 g of p-tert-butylbenzoic acid, in the presence of triethylamine in benzene. Water and chloroform were added to the reaction mixture for extraction. The organic layer was collected and was then washed successively with dilute hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous solution of sodium chloride in the order that they are presented. The solvent was distilled off, whereby 2.42 g of N-methyl-N-(2-phenylbenzyl)-4-tert-butylbenzoic acid amide were obtained as yellow crystals. The acid amide was reduced with lithium aluminum hydride in tetrahydrofuran and the reduction product was extracted with diethyl ether, whereby 0.83 g of 4-tert-butyl-N-methyl-N-(2-phenylbenzyl)benzylamine (Compound 1) was obtained (yield: 35.7%). The following is its NMR spectrum data.

Workup

  1. customThe organic layer was collected
  2. washwas then washed successively with dilute hydrochloric acid
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-a75cb6ce4b254e9790b0708fc0f99d1a
Source dataset
uspto-grants-2000_01
Patent number
US06015925

Reaction notes

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