Triethylamine → HCID 66591737, compound

HRID 2264657Notes

Reaction equation

HRID 2264657 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][NH:17][CH2:18][CH:19]2[CH2:21][CH2:20]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:29][CH2:30][C:31]([NH:33][CH3:34])=[O:32]>CN(C)C=O.Cl.C(OCC)(=O)C>[ClH:29].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][N:17]([CH2:18][CH:19]2[CH2:21][CH2:20]2)[CH2:30][C:31]([NH:33][CH3:34])=[O:32])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 667732-chloro-N-methylacetamideHCID 59596829HCID 59596829, compound

Product 1

HCID 66591737HCID 66591737, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.24 g (0.85 mmol) of [2-(3-benzyloxy-phenyl)-ethyl]-(cyclopropylmethyl)amine, 0.14 ml (1.00 mmol) of triethylamine, 0.11 g (1.02 mmol) of 2-chloro-N-methyl-acetamide in 3 ml of dimethylformamide was heated with microwaves to 120° C. for 2 hours. The solvent was removed and the crude residue was purified by flash chromatography (dichloromethane/methanol/NH3 100:0:0→95:5:0.5 gradient). The product obtained was dissolved in anhydrous hydrochloric acid in ethyl acetate, the solvent was removed under vacuum and the residue was triturated with diethyl ether. 0.24 g (80% yield) of the title compound was isolated as a yellow solid.

Workup

  1. customThe solvent was removed
  2. customthe crude residue was purified by flash chromatography (dichloromethane/methanol/NH3 100:0:0→95:5:0.5 gradient)
  3. customThe product obtained
  4. customthe solvent was removed under vacuum
  5. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-87c2aec7d8414d68adf1113b07fe3d11
Source dataset
uspto-grants-2010_12
Patent number
US07855227B2

Reaction notes

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