Triethylamine → HCID 14304652, compound

HRID 414061Notes

Reaction equation

HRID 414061 reaction equation
S(O[CH2:6][CH2:7][CH2:8][C@@H:9]1[O:14][C:13]2[CH:15]=[C:16]3[C:21](=[CH:22][C:12]=2[NH:11][C:10]1=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17]3)(C)(=O)=O.[F:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:27][CH:26]=1.C(N(CC)CC)C>CN(C)C=O>[F:24][C:25]1[CH:26]=[CH:27][C:28]([N:31]2[CH2:36][CH2:35][N:34]([CH2:6][CH2:7][CH2:8][C@@H:9]3[O:14][C:13]4[CH:15]=[C:16]5[C:21](=[CH:22][C:12]=4[NH:11][C:10]3=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17]5)[CH2:33][CH2:32]2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752601-(4-Fluorophenyl)piperazineHCID 57038968HCID 57038968, compound

Product 1

HCID 14304652HCID 14304652, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-6,7,8,9-tetrahydro-2-(3-mesyloxypropyl)-2H-naphtho[2,3-b][1,4]oxazin-3(4H)-one (1.02g), 1-(4-fluorophenylpiperazine (0.83g), triethylamine (0.43 ml) and dimethylformamide (15 ml) was stirred at 70° C. for 2 hours. The solvent was distilled off and the residue was purified by column chromatography on silica gel (60 g) with ethyl acetate-hexane (3:1, v/v) to yield crystals of (S)-(-)-2-{3-[4-(4-fluorophenyl)-1-piperazinyl]propyl}-6,7,8,9-tetrahydro-2H-naphtho[2,3-b][1,4]oxazin-3(4H)-one (0.76 g, 59.6%). Repeated recrystallization from MeOH gave colorless crystals, m.p. 155.5°-156.6° C. [α]D26 -19.9° (c=1.2, CHCl3).

Workup

  1. distillationThe solvent was distilled off
  2. customthe residue was purified by column chromatography on silica gel (60 g) with ethyl acetate-hexane (3:1

Sources & evidence

ORD record
ord-7d4278d0f9dd46d48e26380e62c8131a
Source dataset
uspto-grants-1988_12
Patent number
US04789675

Reaction notes

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