Ammonia → HCID 89846225, compound

HRID 2278663Notes

Reaction equation

HRID 2278663 reaction equation
C([BH3-])#N.[Na+].[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH:14]=[CH:15][NH:16]3)[CH2:8][CH2:7]1.N>C(O)(=O)C>[CH3:5][N:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH2:14][CH2:15][NH:16]3)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5003444Sodium cyanoborohydrideHCID 220153514-(4-methyl-1-piperazinyl)-1H-indole

Product 1

HCID 89846225HCID 89846225, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
14 °C

Procedure

429 mg of sodium cyanoborohydride are added in portions to a solution of 490 mg of 4-(4-methylpiperazin-1-yl)-1H-indole, in 17 ml of acetic acid cooled to 14° C. The reaction medium is stirred for 2 hours at ambient temperature and then poured into a water/ice mixture and the pH is brought to neutrality with an aqueous ammonia solution. The mixture is then extracted with dichloromethane and the combined organic phases are dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica column chromatography, elution being carried out with a mixture of dichloromethane and methanol (95/05), so as to give 395 mg of 4-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-indole in the form of a colorless viscous oil.

Workup

  1. extractionThe mixture is then extracted with dichloromethane
  2. dry with materialthe combined organic phases are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica column chromatography, elution
  6. additionbeing carried out with a mixture of dichloromethane and methanol (95/05)

Sources & evidence

ORD record
ord-afd705883e634df6ac0a0f61c30def98
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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