Acetic Acid → HCID 22414416, compound

HRID 1721334Notes

Reaction equation

HRID 1721334 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([C:12]1[CH:16]=[CH:15][S:14][C:13]=1[CH3:17])[NH:10][CH3:11].[C:18](O)(=O)[CH3:19].[CH2:22](OC(OCC)(OCC)CC)C>CCCCCC>[CH2:18]([C:11]1[N:10]([CH3:22])[CH:9]([C:12]2[CH:16]=[CH:15][S:14][C:13]=2[CH3:17])[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1)[CH3:19]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 66995Ethyl orthopropionateHCID 22414442HCID 22414442, compound

Product 1

HCID 22414416HCID 22414416, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of 3.95 g of 2-amino-N-methyl-α-(2-methyl-3-thienyl)benzeneethanamine, 5 ml of glacial acetic acid and 17.0 g of triethylorthopropionate was refluxed for 8 hours (under a nitrogen atmosphere). The solution was concentrated in vacuo at 80° C. and the residual oil dissolved in diethyl ether (50 ml) and acidified with 10% hydrochloric acid solution. The aqueous phase was washed with diethyl ether (50 ml), basified, and extracted with dichloromethane (2×100 ml). The combined organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The resultant oil was purified by preparative HPLC (Water's Associates Prep LC/System 500, silica gel, elution with methanol followed by 2% triethylamine in methanol). Concentration of the appropriate fractions afforded 2.26 g of 4,5-dihydro-2-ethyl-3-methyl-4-(2-methyl-3-thienyl)-3H-1,3-benzediazepine as an oil. Trituration with hexane afforded a solid which was combined with product obtained from previous run to afford the analytical sample, mp 82°-83.5° C.

Workup

  1. concentrationThe solution was concentrated in vacuo at 80° C.
  2. dissolutionthe residual oil dissolved in diethyl ether (50 ml)
  3. washThe aqueous phase was washed with diethyl ether (50 ml)
  4. extractionextracted with dichloromethane (2×100 ml)
  5. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resultant oil was purified by preparative HPLC (Water's Associates Prep LC/System 500, silica gel, elution with methanol followed by 2% triethylamine in methanol)
  9. customConcentration of the appropriate fractions afforded 2.26 g of 4,5-dihydro-2-ethyl-3-methyl-4-(2-methyl-3-thienyl)-3H-1,3-benzediazepine as an oil
  10. customobtained from previous run
  11. customto afford the analytical sample, mp 82°-83.5° C.

Sources & evidence

ORD record
ord-b608b3b45a114f1a9dffca9b338e475f
Source dataset
uspto-grants-1996_04
Patent number
US05510346

Reaction notes

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