Dimethylformamide → HCID 17773175, compound

HRID 635332Notes

Reaction equation

HRID 635332 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]3[NH:18][N:19]=[C:20]4[C:25]=3[CH2:24][CH2:23][CH2:22][CH2:21]4)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CN(C)C=O.C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39]>C(OCC)(=O)C.CCCCCC>[C:38]([N:19]1[C:20]2[CH2:21][CH2:22][CH2:23][CH2:24][C:25]=2[C:17]([CH2:16][CH2:15][CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:9][CH2:10]2)=[N:18]1)(=[O:40])[CH3:39]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178505851HCID 178505851, compound

Product 1

HCID 17773175HCID 17773175, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-(3-(4-(4-fluorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydro-2H-indazole (3.1 g), dimethylformamide (30 ml) and triethylamine (2.5 ml) was dropwise added acetyl chloride (0.72 ml) under ice-cooling. The mixture was stirred as it was for 30 minutes. The reaction mixture was poured into ice water (200 ml). The mixture was extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure to give 3.4 g of an oily substance. The oil was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=1:2) to give 0.60 g of 1-acetyl-3-(3-(4-(4-fluorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydro-1H-indazole (component eluted later (compound A)), and 0.30 g of 2-acetyl-3-(3-(4-(4-fluorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydro-2H-indazole (component eluted first (compound B)). 1-Acetyl-3-(3-(4-(4-fluorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydro-1H-indazole (compound A: m.p. 60-61° C.); 2-Acetyl-3-(3-(4-(4-fluorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydro-2H-indazole (compound B: m.p. 104-106° C.).

Workup

  1. temperaturecooling
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give 3.4 g of an oily substance

Sources & evidence

ORD record
ord-976a67049b71489d9e08a318f1031bb1
Source dataset
uspto-grants-2001_02
Patent number
US06187774B1

Reaction notes

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