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Water → HCID 11516226, compound

HRID 743075
Notes
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Reaction equation

HRID 743075 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]=[C:15]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][C:27]=2[NH:28]C(=O)C(Cl)(Cl)Cl)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>C(O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH:15]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][C:27]=2[NH2:28])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]=[C:15]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][C:27]=2[NH2:28])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 19423566HCID 19423566, compound

Product 2

HCID 11516226HCID 11516226, compoundHCID 11516277HCID 11516277, compound

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

Procedure

To a solution of 18.0 g (34.9 mmol) of 3-[α-{(1-benzylpiperidin-4-yl)imino}benzyl]-4-trichloroacetylaminopyridine in 150 mL of ethanol was added 2.65 g (70 mmol) of sodium borohydride under ice-cooling and the mixture was stirred for 5 hours at ambient temperature. The reaction mixture was poured into water, and the ethanol was evaporated in vacuo. The residue was extracted with ethyl acetate. The organic layer separated was washed with water and then with brine, dried on anhydrous sodium sulfate and then concentrated in vacuo. Purification by means of column chromatography (silica gel, 1:9 methanol:chloroform) gave 4.82 g (12.9 mmol) of the title compound and 6.65 g (17.9 mmol) of 3-[α-{(1-benzyl-piperidin-4-yl)imino}benzyl]-4-aminopyridine.

Workup

  1. temperaturecooling
  2. customthe ethanol was evaporated in vacuo
  3. extractionThe residue was extracted with ethyl acetate
  4. customThe organic layer separated
  5. washwas washed with water
  6. dry with materialwith brine, dried on anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification by means of column chromatography (silica gel, 1:9 methanol:chloroform)

Sources & evidence

ORD record
ord-0b0bd4d1bbf34a429811ba0d7e473c53
Source dataset
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05556860

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes