Ethyl fluoroacetate → trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2-fluoroacetamide

HRID 16151

Reaction equation

HRID 16151 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[C@@H:9]3[C@H:14]([NH2:15])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1.[F:22][CH2:23][C:24](OCC)=[O:25]>>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[C@@H:9]3[C@H:14]([NH:15][C:24](=[O:25])[CH2:23][F:22])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 9988Ethyl fluoroacetateHCID 70883458trans-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine

Product 1

HCID 86599860trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2-fluoroacetamideYield 39%

Procedure

trans-7-Chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine (10 mg, 0.03 mmol) was dissolved in 1 mL of ethyl fluoroacetate. The resulting mixture was heated to reflux for 2 h. Evaporation followed by crystallisation from methanol gave trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2-fluoroacetamide (4.7 mg, 39%). Data: (m/z)=361 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 h
  3. customEvaporation
  4. customfollowed by crystallisation from methanol

Sources & evidence

ORD record
ord-9b14aaf8d506412094cc509974542c31
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Linked notes

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