Triethylamine → 2-(4-fluorophenyl)-N-(7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-yl)acetamide

HRID 1819877Notes

Reaction equation

HRID 1819877 reaction equation
C(N(CC)CC)C.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([OH:39])=O)=[CH:32][CH:31]=1.[CH:40]1[C:48]2[C:47]3[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][C:46]=3[O:45][C:44]=2[CH:43]=[CH:42][C:41]=1[NH2:54]>ClCCl>[F:29][C:30]1[CH:31]=[CH:32][C:33]([CH2:36][C:37]([NH:54][C:41]2[CH:42]=[CH:43][C:44]3[O:45][C:46]4[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][C:47]=4[C:48]=3[CH:40]=2)=[O:39])=[CH:34][CH:35]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 98372-(4-Fluorophenyl)acetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 128848837,8,9,10-tetrahydro-6H-benzo[b]-cyclohepta[d]furan-2-ylamine

Product 1

HCID 248999582-(4-fluorophenyl)-N-(7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-yl)acetamideYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.52 mL, 3.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.37 g, 1.9 mmol), N-hydroxybenzotriazole (0.26 g, 1.9 mmol) and 4-fluorophenylacetic acid (0.27 g, 1.8 mmol) were added sequentially to a solution of 7,8,9,10-tetrahydro-6H-benzo[b]-cyclohepta[d]furan-2-ylamine (0.30 g, 1.5 mmol) in dichloromethane (20 mL). The reaction mixture was stirred overnight at ambient temperature and then concentrated. The crude material was dissolved in ethyl acetate and washed with 1 N NaOH and water, dried (MgSO4) and concentrated to give 2-(4-fluorophenyl)-N-(7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-yl)acetamide (0.47 g). MS (ESI) m/z 338 ([M+H]+).

Workup

  1. concentrationconcentrated
  2. dissolutionThe crude material was dissolved in ethyl acetate
  3. washwashed with 1 N NaOH and water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f9963a0d6c4d4157b51638361f4551e8
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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