Triethylamine → HCID 14304651, compound

HRID 414057Notes

Reaction equation

HRID 414057 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH:5]1[O:10][C:9]2[CH:11]=[C:12]3[C:17](=[CH:18][C:8]=2[NH:7][C:6]1=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13]3.[F:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1.C(N(CC)CC)C>CN(C)C=O>[F:20][C:21]1[CH:22]=[CH:23][C:24]([N:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][CH:5]3[O:10][C:9]4[CH:11]=[C:12]5[C:17](=[CH:18][C:8]=4[NH:7][C:6]3=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13]5)[CH2:29][CH2:28]2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752601-(4-Fluorophenyl)piperazineHCID 14304664HCID 14304664, compound

Product 1

HCID 14304651HCID 14304651, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(3-bromopropyl)-6,7,8,9-tetrahydro-2H-naphtho[2,3-b][1,4]oxazin-3(4H)-one (3.1 g), 1-(4-fluorophenyl)piperazine (2.3 g), triethylamine (1.5 ml) and N,N-dimethylformamide (DMF)(100 ml) was stirred at 80° C. for 1.5 hour, which was diluted with ice-water and subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), from which the solvent was distilled off. The residue was recrystallized from chloroform-ethyl acetate to give 2.4 g (59.3%) of 2-{3-[4-(4-fluorophenyl)-1-piperazinyl]propyl}-6,7,8,9-tetrahydro-2H-naphtho[2,3-b][1,4]oxazin-3(4H)-one as colorless crystals, m.p. 164°-165° C.

Workup

  1. extractionsubjected to extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationfrom which the solvent was distilled off
  5. customThe residue was recrystallized from chloroform-ethyl acetate

Sources & evidence

ORD record
ord-5433513a49c44f5e93c52c6feceb4cc5
Source dataset
uspto-grants-1988_12
Patent number
US04789675

Reaction notes

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