1-Benzylpiperidine-4-carbaldehyde → HCID 54153280, compound

HRID 976127Notes

Reaction equation

HRID 976127 reaction equation
C[O-].[Na+].CO.[O:6]=[C:7]1[C:15]2[C:10](=[CH:11][C:12]([NH:16][C:17]3[C:18]4[CH2:25][CH2:24][CH2:23][C:19]=4[N:20]=[CH:21][N:22]=3)=[CH:13][CH:14]=2)[CH2:9][CH2:8]1.[CH2:26]([N:33]1[CH2:38][CH2:37][CH:36]([CH:39]=O)[CH2:35][CH2:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1>[O:6]=[C:7]1[C:15]2[C:10](=[CH:11][C:12]([NH:16][C:17]3[C:18]4[CH2:25][CH2:24][CH2:23][C:19]=4[N:20]=[CH:21][N:22]=3)=[CH:13][CH:14]=2)[CH2:9][C:8]1=[CH:39][CH:36]1[CH2:35][CH2:34][N:33]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 895841-Benzylpiperidine-4-carbaldehydeHCID 19968934HCID 19968934, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 54153280HCID 54153280, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice cooling, 1.70 g of a 28% sodium methoxide·methanol solution was added to 1.96 g of 4-(1-oxoindan-5-yl)amino-5,6-dihydro-7H-cyclopenta[d]pyrimidine dissolved in tetrahydrofuran, and then 1.80 g of 1-benzyl-4-formylpiperidine was added dropwise thereto. After the mixture was stirred for 1.5 hours, a saturated saline solution was added to the reaction mixture, and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and condensed under reduced pressure. The obtained residue was applied to silica gel column chromatography and then recrystallized from chloroform to obtain 1.35 g of the title compound as pale yellow crystal.

Workup

  1. additiona saturated saline solution was added to the reaction mixture
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThe extract was dried over anhydrous sodium sulfate and condensed under reduced pressure
  4. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-2b315716a9d24b1b9b81ced558008e84
Source dataset
uspto-grants-1997_03
Patent number
US05610303

Reaction notes

Loading…