Piperidine → HCID 54188178, compound

HRID 1378122Notes

Reaction equation

HRID 1378122 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:8][C:9]1[O:13][N:12]=[C:11]([C:14]2[N:15]=[CH:16][N:17]3[C:23]4[CH:24]=[CH:25][S:26][C:22]=4[C:21](=[O:27])[N:20]4[CH2:28][CH2:29][C@H:19]4[C:18]=23)[N:10]=1>CN(C)C=O>[N:1]1([CH2:8][C:9]2[O:13][N:12]=[C:11]([C:14]3[N:15]=[CH:16][N:17]4[C:23]5[CH:24]=[CH:25][S:26][C:22]=5[C:21](=[O:27])[N:20]5[CH2:28][CH2:29][C@H:19]5[C:18]=34)[N:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 54112781HCID 54112781, compound

Product 1

HCID 54188178HCID 54188178, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.34 ml (3.45 mmol) of piperidine was added to a suspension of 400 mg (1.15 mmol) of (S)-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-11,11a-dihydro-8H, 10H-azeto[1,2-a]-imidazo[5,1-c]thieno[3,2-e][1,4]diazepin-8-one in 10 ml of N,N-dimethylformamide and the mixture was stirred at room temperature for 12 hours. The solution was evaporated and the residue was partitioned between methylene chloride and 2N sodium carbonate solution. The aqueous solution was extracted with methylene chloride and the organic phases were dried, filtered and evaporated. The residue was chromatographed (silica gel, methyl acetate/methanol 15:1). There were obtained 375 mg (82%) of (S)-1-(5-piperidin-1-ylmethyl-1,2,4-oxadiazol-3-yl)-11,11a-dihydro-8H, 10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e]-[1,4]diazepin-8-one as a colourless foam, Rf=0.22 (silica gel, methyl acetate/methanol 15:1).

Workup

  1. customThe solution was evaporated
  2. customthe residue was partitioned between methylene chloride and 2N sodium carbonate solution
  3. extractionThe aqueous solution was extracted with methylene chloride
  4. customthe organic phases were dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed (silica gel, methyl acetate/methanol 15:1)

Sources & evidence

ORD record
ord-43b8e022933b419aa7dec9bf34c9f52b
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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