4-Indol-1-yl-piperidine-1-carboxylic acid ethyl ester → 1-(1-methyl-piperidin-4-yl)-1H-indole

HRID 1077935Notes

Reaction equation

HRID 1077935 reaction equation
C(O[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)[CH2:8][CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:4][N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 140907494-Indol-1-yl-piperidine-1-carboxylic acid ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 140907431-(1-methyl-piperidin-4-yl)-1H-indoleYield 64.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cooled solution of 4-indol-1-yl-piperidine-1-carboxylic acid ethyl ester (50 g, 0.18 mol) in dry THF (400 mL) was added LAH in small portions (7 g, 0.18 mol). After 2 hours, the mixture was quenched by successive addition of water (7 mL) 15% of sodium hydroxide (7 mL) and water (21 mL). The reaction mixture was filtered. The filtrate was dried and evaporated. The residue crystallized on standing and was recrystallized from a small amount of di-i-propyl ether to give the title compound (25 g, 63% of theory). M.Pt.: 58° C.

Workup

  1. customthe mixture was quenched by successive addition of water (7 mL) 15% of sodium hydroxide (7 mL) and water (21 mL)
  2. filtrationThe reaction mixture was filtered
  3. customThe filtrate was dried
  4. customevaporated
  5. customThe residue crystallized
  6. customwas recrystallized from a small amount of di-i-propyl ether

Sources & evidence

ORD record
ord-6fbfa59307b64db5b2d3839a9d5a3d25
Source dataset
uspto-grants-1996_08
Patent number
US05545636

Reaction notes

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