Hexahydro-1,4-diazepine → HCID 18940424, compound

HRID 355674Notes

Reaction equation

HRID 355674 reaction equation
[Cl:1][C:2]1[C:12]2[O:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[NH:8][C:7](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH:18]1[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>C1(C)C=CC=CC=1.C1(OC)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[C:12]2[O:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[N:8]=[C:7]([N:18]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 186908823158-94-9

Product 1

HCID 18940424HCID 18940424, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolventHCID 7519AnisoleSolvent

Procedure

In a like manner as Example 1, 4-Chloro-10,11-dihydro-dibenz[b,f][1,4]oxazepine-11-one (2.46 g, 10.0 mmol) was reacted with homopiperazine (7.41 g, 74.0 mmol) in the presence of titanium tetrachloride (2.09 g, 11.0 mmol) in toluene (55.0 mL) and anisole (2.00 mL) to produce 4-Chloro-11-(1-homopiperazinyl)dibenz[b,f][1,4]oxazepine; viscous oil; yield, 0.92 g (28%). This crude product (0.26 g, 0.79 mmol) was reacted with 1-bromohexane (0.13 mL, 0.16 g, 0.95 mmol) in the presence of sodium hydride (0.044 mg, 60% in oil, 1.11 mmol) in DMF (10.0 mL) to produce 4-Chloro-11-(4-hexylhomopiperazinyl)dibenz[b,f][1,4]oxazepine; viscous oil; yield, 0.17 g (52%).

Sources & evidence

ORD record
ord-c6ef98c85a61494c88ee58d22c295043
Source dataset
uspto-grants-1998_11
Patent number
US05834459

Reaction notes

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