1-Hexanamine, hydrochloride → HCID 14326777, compound

HRID 2291942Notes

Reaction equation

HRID 2291942 reaction equation
[Cl:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12]([N:15]3[CH2:20][CH2:19][CH2:18][C:17](=O)[CH2:16]3)(=[O:14])=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1.Cl.[CH2:23]([NH2:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C([BH3-])#N.[Na+]>CO>[Cl:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12]([N:15]3[CH2:20][CH2:19][CH2:18][CH:17]([NH:29][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16]3)(=[O:14])=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 673421-Hexanamine, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 14326849HCID 14326849, compound

Product 1

HCID 14326777HCID 14326777, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To 50 ml of methanol were added 2.47 g of the thus obtained 1-(1-chloro-5-isoquinolinesulfonyl)-3-piperidone, 1.11 g of n-hexylamine hydrochloride and 0.50 g of sodium cyanoborohydride, followed by stirring at 20° C. for 15 hours. The methanol was removed under reduced pressure, and 50 ml of chloroform was added to the resultant product. Then, the mixture was washed twice with 50 ml each of water and then washed once with 50 ml of a 50% aqueous sodium hydrogencarbonate solution, and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a residue. The residue thus obtained was subjected to purification by silica gel column chromatography (Wacogel C-200, 100 g; solvent: chloroform) to obtain 2.54 g of 1-(1-chloro-5-isoquinolinesulfonyl)-3-hexylaminopiperidine [Compound (98)]. Compound (98) was analyzed to give the following data.

Workup

  1. customThe methanol was removed under reduced pressure, and 50 ml of chloroform
  2. additionwas added to the resultant product
  3. washThen, the mixture was washed twice with 50 ml each of water
  4. washwashed once with 50 ml of a 50% aqueous sodium hydrogencarbonate solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto obtain a residue
  8. customThe residue thus obtained
  9. customwas subjected to purification by silica gel column chromatography (Wacogel C-200, 100 g; solvent: chloroform)

Sources & evidence

ORD record
ord-7a00454a8ccc4acaab69e7224a352a35
Source dataset
uspto-grants-1989_01
Patent number
US04798897

Reaction notes

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