Water → n-({1-[2-(Benzofuran-3-yl)ethyl]-4-piperidyl}methyl)-n-methylamine

HRID 430603Notes

Reaction equation

HRID 430603 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]([CH2:16][C:17]([N:19]2[CH2:24][CH2:23][CH:22]([C:25]([NH:27][CH3:28])=O)[CH2:21][CH2:20]2)=O)=[CH:8]1.O.[OH-].[Na+]>O1CCCC1>[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]([CH2:16][CH2:17][N:19]2[CH2:20][CH2:21][CH:22]([CH2:25][NH:27][CH3:28])[CH2:23][CH2:24]2)=[CH:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 155123851-(Benzofuran-3-ylacetyl)-n-methyl-4-piperidinecarboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 15512386n-({1-[2-(Benzofuran-3-yl)ethyl]-4-piperidyl}methyl)-n-methylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

7.6 g of lithium aluminium hydride are added in portions to a solution of 28.7 g of the product obtained in Step C in 1.5 litres of tetrahydrofuran heated at 60°C. After 18 hours at reflux, the reaction mixture is hydrolysed by the addition of 5.24 ml of water, 4.2 ml of 20% sodium hydroxide solution and then 19.2 ml of water. After filtration, drying and concentration under reduced pressure, the expected product is isolated. The hydrochloride thereof recrystallises from methanol.

Workup

  1. temperatureAfter 18 hours at reflux
  2. filtrationAfter filtration
  3. customdrying
  4. concentrationconcentration under reduced pressure

Sources & evidence

ORD record
ord-fbfa6618b2eb4e50963005041e31c705
Source dataset
uspto-grants-2001_11
Patent number
US06323217B2

Reaction notes

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