Acetic Acid → N-{6-[4-(Cyclohexylmethyl)piperazin-1-yl]pyridin-3-yl}-4-isopropylbenzenesulfonamide hydrochloride

HRID 444960Notes

Reaction equation

HRID 444960 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[CH:18][CH:19]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH:26]1([CH:32]=O)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:52]CCl>>[ClH:52].[CH:26]1([CH2:32][N:23]2[CH2:22][CH2:21][N:20]([C:17]3[N:16]=[CH:15][C:14]([NH:13][S:10]([C:7]4[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=4)(=[O:11])=[O:12])=[CH:19][CH:18]=3)[CH2:25][CH2:24]2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 16275CyclohexanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 115956504-Isopropyl-N-(6-piperazin-1-ylpyridin-3-yl)benzenesulfonamide

Product 1

HCID 54674787N-{6-[4-(Cyclohexylmethyl)piperazin-1-yl]pyridin-3-yl}-4-isopropylbenzenesulfonamide hydrochloride

Procedure

150 mg (0.42 mmol) of 4-isopropyl-N-(6-piperazin-1-yl-pyridin-3-yl)-benzenesulfonamide from Example 7 and 51 mg (0.46 mmol) of cyclohexanealdehyde were dissolved in 5 ml of dichloromethane and 40 μl (0.62 mmol) of glacial acetic acid under a nitrogen atmosphere. 133 mg (0.63 mmol) of sodium trisacetoxyborohydride were then added. The mixture was stirred at room temperature for 90 minutes and, after that, the solvent was evaporated down to dryness. The resulting residue was taken up in water and this mixture was made to pH>11 with a 1N aqueous solution of sodium hydroxide. After that, the aqueous reaction mixture was extracted with diethyl ether. After the organic phase had been dried over sodium sulfate and the solvent had been filtered and evaporated down to dryness, the resulting residue was converted into the hydrochloride with ethereal hydrochloric acid, resulting in 156 mg (76% of theory) of the title compound.

Workup

  1. customafter that, the solvent was evaporated down to dryness
  2. extractionAfter that, the aqueous reaction mixture was extracted with diethyl ether
  3. dry with materialAfter the organic phase had been dried over sodium sulfate
  4. filtrationthe solvent had been filtered
  5. customevaporated down to dryness

Sources & evidence

ORD record
ord-f750647ba0674ac2859d07e3ec6f0bb0
Source dataset
uspto-grants-2013_07
Patent number
US08476275B2

Reaction notes

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