Sulfuric Acid → HCID 22038029, compound

HRID 1790419Notes

Reaction equation

HRID 1790419 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:5][N:4]=1)#N.[H-].C([Al+]CC(C)C)C(C)C.S(=O)(=O)(O)[OH:37].[OH-].[Na+]>C1(C)C=CC=CC=1.C(OCC)C>[OH:37][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 22037916HCID 22037916, compound

Product 1

HCID 22038029HCID 22038029, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

1-{1-[2-(2-Cyanopyridin-5-yl)ethyl]piperidin-4-yl}indoline (0.103 g) was dissolved in toluene (1.5 ml). In a nitrogen atmosphere at −78° C., a 1.5 M solution (0.44 ml) of diisobutylaluminum hydride in toluene was added thereto and the resultant mixture was stirred under the same conditions for 1 hr. Then the reaction solution was poured into a 5% aqueous solution of sulfuric acid and basified with an aqueous solution of sodium hydroxide. Next, diethyl ether was added and the layers were separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (0.066 g) as a yellow oil (yield: 64.5%).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bb11cc6880ba4d5fa5d7545a818fa5e0
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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