Ethylamine → HCID 12263351, compound

HRID 77514Notes

Reaction equation

HRID 77514 reaction equation
[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=O.Cl.C[N:14](C)[CH2:15][CH2:16]CN=C=NCC.C(N)C>ClCCl>[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([NH:14][CH2:15][CH3:16])=[O:5]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 97919Bromo(phenyl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 12263351HCID 12263351, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.0 g (4.65 mmol) alpha-bromophenylacetic acid (Aldrich), 1.16 g (6.05 mmol) (3-dimethylamino-propyl)-ethyl-carbodiimide hydrochloride (Aldrich), 2.80 mL (5.6 mmol) ethyl-amine (Aldrich, 2 M in dichloromethane) in dichloromethane (30 mL) is stirred at room temperature for 18 h. The reaction mixture is washed with NaOH 1 M (15 mL) and the organic phase is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (gradient: cyclohexane/ethyl acetate 90:10 to 50:50) to yield the title compound (0.32 g, content ca. 90%).

Workup

  1. washThe reaction mixture is washed with NaOH 1 M (15 mL)
  2. customthe organic phase is evaporated under reduced pressure
  3. customThe residue is purified by silica gel column chromatography (gradient: cyclohexane/ethyl acetate 90:10 to 50:50)

Sources & evidence

ORD record
ord-298717dfa0e64392aeb85ef4fa320ad4
Source dataset
uspto-grants-2014_09
Patent number
US08841309B2

Reaction notes

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