Isopropylamine → 1-[2-(3-Carbamoyl-4-hydroxyphenoxy)-1-methylethylamino]-3-(4-methylcarbamoylphenoxy)propan-2-ol

HRID 4530Notes

Reaction equation

HRID 4530 reaction equation
C(N)(C)C.CC1(C)[NH:11][C:10](=[O:12])[C:9]2[CH:13]=[C:14]([O:17][CH2:18][CH:19]([NH:21][CH2:22][CH:23]([OH:36])[CH2:24][O:25][C:26]3[CH:31]=[CH:30][C:29]([C:32](=[O:35])[NH:33][CH3:34])=[CH:28][CH:27]=3)[CH3:20])[CH:15]=[CH:16][C:8]=2[O:7]1>CO>[C:10]([C:9]1[CH:13]=[C:14]([CH:15]=[CH:16][C:8]=1[OH:7])[O:17][CH2:18][CH:19]([NH:21][CH2:22][CH:23]([OH:36])[CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:35])[NH:33][CH3:34])=[CH:28][CH:27]=1)[CH3:20])(=[O:12])[NH2:11]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 201513441-[2-(2,3-dihydro-2,2-dimethyl-4-oxo-4H-1,3-benzoxazin-6-yloxy)-1-methylethylamino]-3-(4-methylcarbamoylphenoxy)propan-2-ol

Product 1

HCID 137543661-[2-(3-Carbamoyl-4-hydroxyphenoxy)-1-methylethylamino]-3-(4-methylcarbamoylphenoxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

80 ml of isopropylamine are added to a solution of 18.0 g of crude 1-[2-(2,3-dihydro-2,2-dimethyl-4-oxo-4H-1,3-benzoxazin-6-yloxy)-1-methylethylamino]-3-(4-methylcarbamoylphenoxy)propan-2-ol in 300 ml of methanol and the solution is refluxed for 1 hour. The reaction mixture is concentrated by evaporation and the oil remaining is crystallised from 80 ml of isopropanol. 1-[2-(3-Carbamoyl-4-hydroxyphenoxy)-1-methylethylamino]-3-(4-methylcarbamoylphenoxy)propan-2-ol having a melting point of 172°-175° (diastereoisomeric mixture) is obtained.

Workup

  1. temperaturethe solution is refluxed for 1 hour
  2. concentrationThe reaction mixture is concentrated by evaporation
  3. customthe oil remaining is crystallised from 80 ml of isopropanol

Sources & evidence

ORD record
ord-3d6d6e38432d46b8a8a0b5dc77aff31a
Source dataset
uspto-grants-1988_02
Patent number
US04727067

Reaction notes

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