Thionyl Chloride → HCID 13282023, compound

HRID 2295294Notes

Reaction equation

HRID 2295294 reaction equation
[CH:1]1[S:2][CH:3]=[C:4]2[C:10]=1[C:9](=[O:11])[NH:8][C:7]1[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=1[NH:5]2.[CH3:16][N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][C:24](Cl)=[O:25])[CH2:19][CH2:18]1.[K].CN1CCC(CC(O)=O)CC1.S(Cl)(Cl)=O>O1CCOCC1.N1C=CC=CC=1.O>[CH3:16][N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][C:24]([N:5]2[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[NH:8][C:9](=[O:11])[C:10]3=[CH:1][S:2][CH:3]=[C:4]23)=[O:25])[CH2:19][CH2:18]1

Participants

9

Reactant 5

HCID 24386Thionyl ChlorideHCID 428619(1-Methylpiperidin-4-yl)acetic acidHCID 5462222PotassiumHCID 125216414,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-oneHCID 13282022(1-Methylpiperidin-4-yl)acetyl chloride

Product 1

HCID 13282023HCID 13282023, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent3×

Conditions

Temperature
40 °C

Procedure

A solution of 2.2 gm (0.01 mol) of 4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 50 ml of dioxane and 10 ml of pyridine was mixed at ambient temperature with a solution of 0.02 mol of (1-methyl-4-piperidinyl)acetyl chloride (prepared from the potassium salt of 1-methyl-4-piperidinylacetic acid by reaction with thionyl chloride) in 100 ml of dioxane. The mixture was heated at 40° C. for three hours, with stirring, and then at 80° C. for two hours. After the dioxane solution was poured off, the viscous residue was taken up in water, the resulting mixture was filtered, and the filtrate was rendered alkaline and extracted with methylene chloride. The extraction residue was purified by column chromatography [silica gel, eluant: ethyl acetate/methylene chloride (1:1); then with methylene chloride/cyclohexane/methanol/ammonia (102:23:23:3) as eluant]. The desired fraction was concentrated by evaporation in vacuo and the residue was recrystallized from ethyl acetate.

Workup

  1. filtrationthe resulting mixture was filtered
  2. extractionextracted with methylene chloride
  3. customThe extraction residue was purified by column chromatography [silica gel, eluant
  4. concentrationThe desired fraction was concentrated by evaporation in vacuo
  5. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b92e941533fe4951b3909e120b02ae5a
Source dataset
uspto-grants-1984_01
Patent number
US04424225

Reaction notes

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