Acetic Acid → HCID 68654647, compound

HRID 1944659Notes

Reaction equation

HRID 1944659 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([CH:19]=O)C=C[C:13]=3[N:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH3:21][C:22](O)=O.N1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.[BH3-][C:32]#N.[Na+]>C1COCC1>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([N:28]4[CH2:29][CH2:30][CH2:32][CH2:26][CH2:27]4)[CH:19]=[C:22]([CH3:21])[C:13]=3[N:14]=2)[CH2:8][CH2:9]1)([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4837PiperazineHCID 5003444Sodium cyanoborohydrideHCID 59588785HCID 59588785, compound

Product 1

HCID 68654647HCID 68654647, compoundYield 257.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
63 °C

Procedure

To a solution of 2-(4-isopropylpiperazin-1-yl)benzothiazole-6-carboxaldehyde (0.5 g, 1.73 mmol) and AcOH (11 mg, 0.173 mmol) in THF (5 mL), piperazine (0.34 ml, 3.46 mmol) and NaCNBH3 (132 mg, 2.08 mmol) were added in turn. The reaction mixture was heated at 63° C. for 12 hours. The solvent was removed and the mixture was extracted with ethyl acetate, washed with water and brine and dried (MgSO4). The volatiles were evaporated and the residue was purified by column chromatography on silica gel, eluting with ethyl acetate and methanol (10:1) to yield 160 mg (26%) of 2-(4-isopropylpiperazin-1-yl)-6-piperidin-1-yl-methylbenzothiazole.

Workup

  1. customThe solvent was removed
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customThe volatiles were evaporated
  6. customthe residue was purified by column chromatography on silica gel
  7. washeluting with ethyl acetate and methanol (10:1)

Sources & evidence

ORD record
ord-ad9833ea7c944b3396d357f5e08e3a20
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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