4-(2,3-epoxypropoxy)-N-methylbenzamide → 1-[N-[2-(2,3-dihydro-2,2-dimethyl-4-oxo-4H-1,3-benzoxazin-6-yloxy)-1-methylethyl]benzylamino]-3-(4-methylcarbamoylphenoxy)propan-2-ol

HRID 615219Notes

Reaction equation

HRID 615219 reaction equation
[CH2:1]([NH:8][CH:9]([CH3:25])[CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[O:20][C:19]([CH3:22])([CH3:21])[NH:18][C:17](=[O:23])[C:16]=2[CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:26]1[CH2:40][CH:27]1[CH2:28][O:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([NH:36][CH3:37])=[O:35])=[CH:32][CH:31]=1>C(O)(C)C>[CH3:21][C:19]1([CH3:22])[NH:18][C:17](=[O:23])[C:16]2[CH:24]=[C:12]([O:11][CH2:10][CH:9]([N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:40][CH:27]([OH:26])[CH2:28][O:29][C:30]3[CH:39]=[CH:38][C:33]([C:34](=[O:35])[NH:36][CH3:37])=[CH:32][CH:31]=3)[CH3:25])[CH:13]=[CH:14][C:15]=2[O:20]1

Participants

4

Reactant 2

HCID 122382484-(2,3-epoxypropoxy)-N-methylbenzamideHCID 137544146-(2-benzylaminopropoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one

Product 1

HCID 543947081-[N-[2-(2,3-dihydro-2,2-dimethyl-4-oxo-4H-1,3-benzoxazin-6-yloxy)-1-methylethyl]benzylamino]-3-(4-methylcarbamoylphenoxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 13.6 g of 6-(2-benzylaminopropoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one and 10.4 g of 4-(2,3-epoxypropoxy)-N-methylbenzamide in 80 ml of isopropanol is refluxed for 30 hours. The residue remaining after the solvent has been evaporated off is divided between ether and 2N hydrochloric acid. The acidic, aqueous phase is separated off, and, whilst cooling with ice, rendered alkaline with approximately 10% aqueous ammonia solution and extracted with ethyl acetate. By separating off, drying (MgSO4) and concentrating the ethyl acetate extract by evaporation, the crude 1-[N-[2-(2,3-dihydro-2,2-dimethyl-4-oxo-4H-1,3-benzoxazin-6-yloxy)-1-methylethyl]benzylamino]-3-(4-methylcarbamoylphenoxy)propan-2-ol is obtained as an oil which may be used without further purification for catalytic debenzylation.

Workup

  1. customhas been evaporated off
  2. customThe acidic, aqueous phase is separated off
  3. temperaturewhilst cooling with ice
  4. extractionextracted with ethyl acetate
  5. customBy separating off
  6. dry with materialdrying (MgSO4)
  7. concentrationconcentrating the ethyl acetate
  8. extractionextract by evaporation

Sources & evidence

ORD record
ord-3f60ceb6a00a458a859a5d314196c66b
Source dataset
uspto-grants-1985_02
Patent number
US04497813

Reaction notes

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