Ethyl alpha-oxobenzenebutanoate → 3-[N-(1-carboethoxy-3-phenylpropyl)amino]-5-methyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

HRID 1632779Notes

Reaction equation

HRID 1632779 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[N:4]([CH3:14])[CH2:3]1.O=[C:16]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[C:17]([CH:16]([NH:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[N:4]([CH3:14])[CH2:3]1)[CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([O:19][CH2:20][CH3:21])=[O:18]

Participants

6

Reactant 3

HCID 562087Ethyl alpha-oxobenzenebutanoateHCID 5003444Sodium cyanoborohydrideHCID 204423323-Amino-5-methyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2-one

Product 1

HCID 204423303-[N-(1-carboethoxy-3-phenylpropyl)amino]-5-methyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

The 3-amino-5-methyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2-one (0.267 g) is dissolved in 5 ml of methanol and 0.288 g of ethyl 2-oxo-4-phenylbutyrate is added. This is followed by the addition of a solution of 88 mg of sodium cyanoborohydride in 3 ml of methanol and 0.8 ml of glacial acetic acid. The reaction is stirred overnight under nitrogen and concentrated. The residue is dissolved in 20 ml of methylene chloride and washed with 10 ml of cold saturated sodium carbonate. After drying over magnesium sulfate the solution is concentrated and the residue purified to give 3-[N-(1-carboethoxy-3-phenylpropyl)amino]-5-methyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in 20 ml of methylene chloride
  3. washwashed with 10 ml of cold saturated sodium carbonate
  4. dry with materialAfter drying over magnesium sulfate the solution
  5. concentrationis concentrated
  6. customthe residue purified

Sources & evidence

ORD record
ord-917fe34274cf4ee5ac1512e28f4bf307
Source dataset
uspto-grants-1984_10
Patent number
US04477464

Reaction notes

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