Acetaldehyde → HCID 10831852, compound

HRID 361866Notes

Reaction equation

HRID 361866 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:25]([CH3:27])[CH3:26])[C:15]2[C:20]([NH:21][CH:22](C)[CH3:23])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)C.C([BH3-])#N.[Na+].[OH-].[Na+]>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:25]([CH3:26])[CH3:27])[C:15]2[C:20]([NH:21][CH2:22][CH3:23])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 53676689HCID 53676689, compound

Product 1

HCID 10831852HCID 10831852, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-benzyl-4-[N-isopropyl-N-(3-amino-2-pyridinyl)amino]piperidine (EXAMPLE 101, after titanium chloride reduction of nitro group; 1.92 g) is dissolved in 15 ml of methanol and cooled to 0°. Then 0.5 ml of acetaldehyde and 0.56 g of sodium cyanoborohydride are added. The reaction is allowed to warm slowly to 20°-25° and stirred for 15 hr. Then it is poured into sodium hydroxide (1N) and extracted with chloroform. The extracts are dried over sodium sulfate, and concentrated under reduced pressure. Purification by flash column chromatography (20% ethyl acetate/hexane) gives the title compound.

Workup

  1. temperaturecooled to 0°
  2. temperatureto warm slowly to 20°-25°
  3. extractionextracted with chloroform
  4. dry with materialThe extracts are dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-87e8f5e3399f479082a3de4bd98fcf22
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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