Pyridine → HCID 86699286, compound

HRID 2278661Notes

Reaction equation

HRID 2278661 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[CH3:16][S:17]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)(=[O:19])=[O:18].N1C=CC=CC=1.[NH:32]1[C:40]2[CH:39]=[CH:38][CH:37]=[C:36]([CH:41]=O)[C:35]=2[CH:34]=[CH:33]1>O1CCCC1>[CH3:16][S:17]([N:20]1[CH2:25][CH2:24][N:23]([CH2:41][C:36]2[CH:37]=[CH:38][CH:39]=[C:40]3[C:35]=2[CH2:34][CH2:33][NH:32]3)[CH2:22][CH2:21]1)(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 1049PyridineHCID 333703Indole-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 162656121-Methanesulfonylpiperazine hydrochloride

Product 1

HCID 86699286HCID 86699286, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.92 g of sodium triacetoxyborohydride, 2.26 of 1-methanesulfonylpiperazine hydrochloride and 545 mg of pyridine are successively added to a solution of 1 g of indole-4-carboxaldehyde in 40 ml of tetrahydrofuran under argon. The reaction mixture is stirred at ambient temperature for 15 hours, and then concentrated under reduced pressure. The residue is taken up in 40 ml of acetic acid cooled to 15° C., and then 1.30 g of sodium cyanoborohydride are added in portions. The reaction medium is stirred for 2 hours while allowing it to rise to ambient temperature, poured into a water/ice mixture, treated with 28% aqueous ammonia until the pH is neutral, and extracted with dichloromethane (4×30 ml). The organic phases are combined, dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue obtained is purified on a silica column (eluent: heptane/ethyl acetate, from 0 to 100% of ethyl acetate), so as to give 890 mg of 4-(4-methanesulfonylpiperazin-1-ylmethyl)-2,3-dihydro-1H-indole in the form of a yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. temperaturecooled to 15° C.
  3. addition1.30 g of sodium cyanoborohydride are added in portions
  4. stirringThe reaction medium is stirred for 2 hours
  5. customto rise to ambient temperature
  6. additionpoured into a water/ice mixture
  7. additiontreated with 28% aqueous ammonia until the pH
  8. extractionextracted with dichloromethane (4×30 ml)
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue obtained
  13. customis purified on a silica column (eluent: heptane/ethyl acetate, from 0 to 100% of ethyl acetate)

Sources & evidence

ORD record
ord-18cebe1098e24d439a5bdd5312eb2cfc
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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