Phenyl isocyanate → N-Phenyl-4-(5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine-11-yl)-1-piperidine carboxamide

HRID 2119016Notes

Reaction equation

HRID 2119016 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH:7]2[C:13]3=[CH:14][CH:15]=[CH:16][N:12]3[CH2:11][C:10]3[CH:17]=[CH:18][CH:19]=[CH:20][C:9]=3[O:8]2)[CH2:3][CH2:2]1.[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1C=CC=CC=1>[C:21]1([NH:27][C:28]([N:1]2[CH2:2][CH2:3][CH:4]([CH:7]3[C:13]4=[CH:14][CH:15]=[CH:16][N:12]4[CH2:11][C:10]4[CH:17]=[CH:18][CH:19]=[CH:20][C:9]=4[O:8]3)[CH2:5][CH2:6]2)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 1368935811-(piperdin-4-yl)-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine

Product 1

HCID 13689412N-Phenyl-4-(5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine-11-yl)-1-piperidine carboxamideYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 11-(piperidin-4-yl)-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine (4.8 g, 0.018 mole) and phenylisocyanate (2.14 ml, 0.02 mole) in 140 ml benzene was heated at 65° C. for 1 hour. The reaction mixture was then cooled. The product was filtered and dried to yield 6.25 g (90%) of a solid, m.p. 184°-192° C. This was recrystallized from tetrahydrofuran/diethyl ether (1:4) to yield 5.9 g (85%) of an analytically pure solid, m.p. 167°-170° C.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. filtrationThe product was filtered
  3. customdried

Sources & evidence

ORD record
ord-a9390ddc73cd45499f86732182627d75
Source dataset
uspto-grants-1987_07
Patent number
US04681879

Reaction notes

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