2-(4-Methoxyphenyl)-1,1-dimethylethylamine → 5-benzyloxy-8-{1-hydroxy-2-[2-(4-methoxy-phenyl)-1,1-dimethyl-ethylimino]-ethyl}-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

HRID 969470Notes

Reaction equation

HRID 969470 reaction equation
[CH2:1]([O:8][C:9]1[C:14]2[NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[O:18][C:13]=2[C:12]([C:22](=[O:28])[CH:23](OCC)O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][C:38]([NH2:41])([CH3:40])[CH3:39])=[CH:33][CH:32]=1>C(O)C>[CH2:1]([O:8][C:9]1[C:14]2[NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[O:18][C:13]=2[C:12]([CH:22]([OH:28])[CH:23]=[N:41][C:38]([CH3:39])([CH3:40])[CH2:37][C:34]2[CH:35]=[CH:36][C:31]([O:30][CH3:29])=[CH:32][CH:33]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 918922-(4-Methoxyphenyl)-1,1-dimethylethylamineHCID 590172615-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 694612895-benzyloxy-8-{1-hydroxy-2-[2-(4-methoxy-phenyl)-1,1-dimethyl-ethylimino]-ethyl}-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.1 g (26 mmol) 5-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one and 4 g (22 mmol) 2-(4-methoxy-phenyl)-1,1-dimethyl-ethylamine are stirred in 100 ml of ethanol for 2 hours at 60 to 70° C. After some of the solvent has been distilled off a solid is precipitated out during cooling, and this is suction filtered and washed with ethanol and diethyl ether.

Workup

  1. distillationAfter some of the solvent has been distilled off a solid
  2. customis precipitated out
  3. temperatureduring cooling
  4. filtrationthis is suction filtered
  5. washwashed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-7f2f0bfcb6e441fa9c0bc26283c68834
Source dataset
uspto-grants-2007_12
Patent number
US07307076B2

Reaction notes

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