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4-Methylmorpholine → 1-methyl-2-[(2-methylpropoxy)carbonyl]-amino-methyl-5-(2'-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine

HRID 1591259
Notes
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Reaction equation

HRID 1591259 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[N:5][CH2:4][CH:3]1[CH2:20]N.Cl[C:23]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:24].C[N:31]1CCOCC1>C(Cl)Cl>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[N:5][CH:4]([NH2:31])[C:3]1([CH3:20])[C:23]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 14510005(5-(2-fluorophenyl)-1-methyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-2-yl)methanamine

Product 1

HCID 867467511-methyl-2-[(2-methylpropoxy)carbonyl]-amino-methyl-5-(2'-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepineYield 68.2%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

According to the method of Example 1, 1-methyl-2-aminomethyl-5-(2'-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine (250 mg, 0.88 mmole) and isobutyl chloroformate (114 μl, 0.88 mmole) were combined with 4 ml of dry methylene chloride, and 97 μl of N-methyl-morpholine (0.88 mmole) at -5° C. was added to the mixture. The resulting reaction mixture was allowed to warm to room temperature over 2 hours, and after dilution and washing, rotoevaporation of the dried extracts of the reaction afforded 230 mg of an oil which was purified by silica gel chromatography (ethyl acetate-hexane elution, 7:3 v/v) to give the analytical sample (120 mg) which was 98% pure by HPLC.

Workup

  1. additionwas added to the mixture
  2. customThe resulting reaction mixture
  3. washafter dilution and washing

Sources & evidence

ORD record
ord-990bfaf8fb0c420b812d1032acbf0804
Source dataset
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05206238

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes