Triethylamine → HCID 59596851, compound

HRID 2264672Notes

Reaction equation

HRID 2264672 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][NH:17][CH:18]2[CH2:22][CH2:21][O:20][CH2:19]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[CH2:31][C:32]([N:34]([CH3:36])[CH3:35])=[O:33]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][N:17]([CH:18]2[CH2:22][CH2:21][O:20][CH2:19]2)[CH2:31][C:32]([N:34]([CH3:36])[CH3:35])=[O:33])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 758862-chloro-N,N-dimethylacetamideHCID 59596819HCID 59596819, compound

Product 1

HCID 59596851HCID 59596851, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.8 g (2.69 mmol) of [2-(3-benzyloxy-phenyl)-ethyl]-(tetrahydrofuran-3-yl)amine, 0.56 ml (4.03 mmol) of triethylamine and 0.415 ml (4.03 mmol) of 2-chloro-N,N-dimethyl-acetamide in 5 ml of dry dimethylformamide was heated to 120° C. for 2 hours with microwaves. Solvent was removed under vacuum and the crude residue was purified by flash chromatography (dichloromethane/methanol: 100:3, v:v). 0.611 g (59% yield) of the title compound were isolated as a yellow oil.

Workup

  1. customSolvent was removed under vacuum
  2. customthe crude residue was purified by flash chromatography (dichloromethane/methanol: 100:3, v:v)

Sources & evidence

ORD record
ord-e5d48718699047e0a12fb4c98a912cdf
Source dataset
uspto-grants-2010_12
Patent number
US07855227B2

Reaction notes

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