Water → 1-[1-(4-Aminomethylphenethyl)piperidin-4-yl]indoline

HRID 1790409Notes

Reaction equation

HRID 1790409 reaction equation
O[N:2]=[CH:3][C:4]1[CH:26]=[CH:25][C:7]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 738613811-[1-(4-Hydroxyiminomethylphenethyl)piperidin-4-yl]indoline

Product 1

HCID 220382211-[1-(4-Aminomethylphenethyl)piperidin-4-yl]indolineYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[1-(4-Hydroxyiminomethylphenethyl)piperidin-4-yl]indoline (2.71 g) was dissolved in tetrahydrofuran (40 ml). Under ice cooling, lithium aluminum hydride (0.59 g) was added thereto and the resultant mixture was heated under reflux for 2 hr. Then the reaction mixture was ice cooled again followed by the addition of water (0.6 ml), a 5 N aqueous solution (0.6 ml) of sodium hydroxide and further water (1.8 ml) thereto. The resulting precipitate was filtered off and the filtrate was washed with ethyl acetate and concentrated under reduced pressure to give the title compound (1.462 g) as a pale yellow oil (yield: 56.2%).

Workup

  1. temperatureunder reflux for 2 hr
  2. temperaturecooled again
  3. filtrationThe resulting precipitate was filtered off
  4. washthe filtrate was washed with ethyl acetate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98ebcd9e97ca4f119dabd45ea7c19bd3
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

Loading…