Water → HCID 68109384, compound

HRID 404563Notes

Reaction equation

HRID 404563 reaction equation
C([Li])CCC.[NH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:12][Si:13]([CH3:23])([CH:21]=[CH2:22])[C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.O>C1COCC1>[CH3:12][Si:13]([CH3:23])([CH2:21][CH2:22][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 68109500HCID 68109500, compoundHCID 178418339Butyllithium

Product 1

HCID 68109384HCID 68109384, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

At 50° C., n-butyl lithium (8 ml/L, 21 ml) was slowly added dropwise into the THF solution of piperidine (3.5 g, 41 mmol). After the solution was stirred at 50° C. for 30 minutes, compound 6c (0.6 g, 3.4 mmol) in THF was slowly added into the reaction mixture. After the reaction mixture was stirred at 50° C. for 2 hours, three times of water was added into the reaction solution, followed by extracted with ethyl acetate. The organic layer was dried and evaporated to give a crude product, which was purified using column chromatography to give the product.

Workup

  1. stirringAfter the reaction mixture was stirred at 50° C. for 2 hours
  2. extractionby extracted with ethyl acetate
  3. customThe organic layer was dried
  4. customevaporated

Sources & evidence

ORD record
ord-4b9a647bf0b9464389fc68e4cad0db75
Source dataset
uspto-grants-2014_06
Patent number
US08748610B2

Reaction notes

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