Phenethylamine → HCID 17178178, compound

HRID 2414013Notes

Reaction equation

HRID 2414013 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([OH:13])=O)=[CH:7][CH:6]=1)=[O:4].[C:14]1([CH2:20][CH2:21][NH2:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[C:14]1([CH2:20][CH2:21][NH:22][C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=2)=[O:13])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 15513Monomethyl terephthalate

Product 1

HCID 17178178HCID 17178178, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N'-Carbonyldiimidazole (16.2 g, 0.1 mole) was added portionwise under nitrogen to 1,4-benzenedicarboxylic acid monomethyl ester (18 g, 0.1 mole) in dry dichloromethane (250 ml) and stirred for 1 hour. Benzeneethanamine (12.1 g, 0.1 mole) was added and the reaction stirred for 3 hours. The solution was washed with dilute hydrochloric acid, aqueous sodium bicarbonate solution and water, dried and evaporated. The residue, on trituration with ether, afforded the sub-title compound (23.8 g) as a white solid mp 148°.

Workup

  1. stirringthe reaction stirred for 3 hours
  2. washThe solution was washed with dilute hydrochloric acid, aqueous sodium bicarbonate solution and water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-c7e4a0c653724c4f963c28d1eebd5e8a
Source dataset
uspto-grants-1988_01
Patent number
US04720586

Reaction notes

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