Triethylamine → HCID 11291209, compound

HRID 346455Notes

Reaction equation

HRID 346455 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[CH:16]=[CH:15][NH:14][C:13](=[O:17])[CH2:12][C:11]=2[CH:18]=1.C(N(CC)CC)C.[CH3:29][O:30][CH2:31][C:32](Cl)=[O:33]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[CH:16]=[CH:15][N:14]([C:32](=[O:33])[CH2:31][O:30][CH3:29])[C:13](=[O:17])[CH2:12][C:11]=2[CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 112545798-(3-Fluoro-benzyloxy)-1,3-dihydro-benzo[d]azepin-2-one

Product 1

HCID 11291209HCID 11291209, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a dried flask under an inert atmosphere, 50 mg (0.18 mmol) of 8-(3-fluoro-benzyloxy)-1,3-dihydro-benzo[d]azepin-2-one were dissolved in 3 ml of dichloromethane, and the solution cooled to 0° C. Thereupon, 21 mg (0.21 mmol) triethylamine were added and stirring continued at 0° C. Finally, 18 μl (0.2 mmol) of methoxyacetic acid chloride were added. The reaction mixture was left to warm to RT and stirring continued for 18 h. For the working-up, the reaction mixture was evaporated under reduced pressure. For purification, the crude material obtained was directly transferred on a column and chromatographed on silica gel using a 99:1-mixture of dichloromethane and methanol as the eluent. There were obtained 15 mg (24% of theory) of 8-(3-fluoro-benzyloxy)-3-methoxyacetyl-1,3-dihydro-benzo[d]azepin-2-one as a white powder; MS: m/e=356 (M+H)+.

Workup

  1. customcontinued at 0° C
  2. waitThe reaction mixture was left
  3. temperatureto warm to RT
  4. stirringstirring
  5. customthe reaction mixture was evaporated under reduced pressure
  6. customFor purification
  7. customthe crude material obtained
  8. customchromatographed on silica gel using a 99

Sources & evidence

ORD record
ord-edb1158dbccb428e94ba3eb9b7c7725b
Source dataset
uspto-grants-2007_02
Patent number
US07173023B2

Reaction notes

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