Sodium borohydride → N-formyl-N-methyl-2-methylamino-alpha-(3-methyl-2-thienyl)benzeneethanamine

HRID 486668Notes

Reaction equation

HRID 486668 reaction equation
O=C1CCC(=O)N1[CH2:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH:17]([C:22]1[S:23][CH:24]=[CH:25][C:26]=1[CH3:27])[N:18]([CH:20]=[O:21])[CH3:19].[BH4-].[Na+]>CS(C)=O>[CH:20]([N:18]([CH3:19])[CH:17]([C:22]1[S:23][CH:24]=[CH:25][C:26]=1[CH3:27])[CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][CH3:8])=[O:21]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 104526792-[(2,5-dioxo-1-pyrrolidinyl)methyl]amino-N-formyl-N-methyl-alpha-(3-methyl-2-thienyl)benzeneethanamine

Product 1

HCID 11778875N-formyl-N-methyl-2-methylamino-alpha-(3-methyl-2-thienyl)benzeneethanamine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 6.39 g of 2-[(2,5-dioxo-1-pyrrolidinyl)methyl]amino-N-formyl-N-methyl-α-(3-methyl-2-thienyl)benzeneethanamine, 20 ml of anhydrous dimethyl sulfoxide and 0.72 g of sodium borohydride was stirred at ambient temperature for 15 minutes and then heated on a steam bath for 15 minutes with occasional agitation. After standing for 2 hours at ambient temperature, the reaction mixture was decanted into 150 ml of water and extracted with diethyl ether (2×100 ml). The organic phase was washed with water (2×100 ml), dried over anhydrous sodium sulfate, and concentrated to an oil. Thin layer chromatography of the resultant oil indicated a multi-component mixture. Purification of the mixture was accomplished by HPLC (Waters Associates Prep LC/System 500, silica gel, elution with methanol]. Concentration of the appropriate fractions afforded N-formyl-N-methyl-2-methylamino-α-(3-methyl-2-thienyl)benzeneethanamine) as an oil.

Workup

  1. temperatureheated on a steam bath for 15 minutes with occasional agitation
  2. waitAfter standing for 2 hours at ambient temperature
  3. customthe reaction mixture was decanted into 150 ml of water
  4. extractionextracted with diethyl ether (2×100 ml)
  5. washThe organic phase was washed with water (2×100 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to an oil
  8. customPurification of the mixture
  9. washWaters Associates Prep LC/System 500, silica gel, elution with methanol]

Sources & evidence

ORD record
ord-eb1a86afe3794cad80b47b6b653a8167
Source dataset
uspto-grants-1994_03
Patent number
US05292760

Reaction notes

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