Sodium Carbonate → 9,10-dihydro-4-(pyrrolidinoacetyl)-4H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 1702445Notes

Reaction equation

HRID 1702445 reaction equation
Cl[CH2:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8](=[O:16])[C:7]2=[CH:17][S:18][CH:19]=[C:6]12)=[O:4].[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[N:20]1([CH2:2][C:3]([N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][C:8](=[O:16])[C:7]3=[CH:17][S:18][CH:19]=[C:6]23)=[O:4])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 31268PyrrolidineHCID 200638994-chloroacetyl-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 205038009,10-dihydro-4-(pyrrolidinoacetyl)-4H-thieno[3,4-b][1,5]benzodiazepin-10-oneYield 65.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.9 g of 4-chloroacetyl-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one, 0.55 g of pyrrolidine, 0.85 g of ground sodium carbonate and 15 ml of absolute ethanol are heated at the boil for 2 hours, and the resulting hot solution is filtered and concentrated in vacuo. The obtained residue is dissolved in methylene chloride; the organic solution is washed at pH 7 with water and then concentrated; 1.4 g of 9,10-dihydro-4-(pyrrolidinoacetyl)-4H-thieno[3,4-b][1,5]benzodiazepin-10-one are thus obtained.

Workup

  1. filtrationthe resulting hot solution is filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe obtained residue is dissolved in methylene chloride
  4. washthe organic solution is washed at pH 7 with water
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7bef6354b9274bbcb0993a62a9967076
Source dataset
uspto-grants-1983_04
Patent number
US04381301

Reaction notes

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