N-(2,6-difluorobenzoyl)-3-amino-3-(4-chlorophenyl) 1-propanol → 2-(2-chloro-6-fluorophenyl)-4-phenyl-5,6-dihydro(4H)1,3-oxazine

HRID 1276214Notes

Reaction equation

HRID 1276214 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:3]=1[C:4]([NH:6][CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:8][CH2:9][OH:10])=O.FC1C=CC=C(F)C=1C(NC(C1C=CC(Cl)=CC=1)CCO)=O>>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:3]=1[C:4]1[O:10][CH2:9][CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1

Participants

3

Reactant 2

HCID 15790732N-(2,6-difluorobenzoyl)-3-amino-3-(4-chlorophenyl) 1-propanolHCID 22115251N-(2-chloro-6-fluorobenzoyl)-3-amino-3-phenyl-1-propanol

Product 1

HCID 221152542-(2-chloro-6-fluorophenyl)-4-phenyl-5,6-dihydro(4H)1,3-oxazineYield 66.8%

Procedure

The procedure is as for Example 85, but 3.5 g (11.4 mmol) of N-(2-chloro-6-fluorobenzoyl)-3-amino-3-phenyl-1-propanol are employed instead of N-(2,6-difluorobenzoyl)-3-amino-3-(4-chlorophenyl)-1-propanol. 2.2 g (66.8%) of 2-(2-chloro-6-fluorophenyl)-4-phenyl-5,6-dihydro(4H)1,3-oxazine are obtained as a colorless oil.

Sources & evidence

ORD record
ord-d4e0acd845c64e9599a087c260349102
Source dataset
uspto-grants-2000_12
Patent number
US06166010

Reaction notes

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