Water → Ethyl 4-(1H-indol-3-yl)piperidine-1-carboxylate

HRID 457781Notes

Reaction equation

HRID 457781 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:3][CH2:2]1.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18].O>ClCCl>[CH2:20]([O:19][C:17]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:3][CH2:2]1)=[O:18])[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 10928Ethyl chloroformateHCID 7022353-(4-Piperidinyl)-1H-indole

Product 1

HCID 11380267Ethyl 4-(1H-indol-3-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 30 g (0.15 mol) of 3-piperidin-4-yl-1H-indole and 28 mL (0.2 mol) in 185 mL of anhydrous dichloromethane, 17 mL (0.18 mol) of ethyl chloroformate was added dropwise keeping the temperature of the reaction below 20° C. After 2 h at room temperature, the crude mixture was poured into 100 mL of water. The organic layer was separated and dried with sodium sulfate. After filtration, the solvent was removed under reduced pressure affording 39 g (95% of yield) of the expected product.

Workup

  1. customthe temperature of the reaction below 20° C
  2. customThe organic layer was separated
  3. dry with materialdried with sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was removed under reduced pressure
  6. customaffording

Sources & evidence

ORD record
ord-1a21629110c444ad9f846d0e44f99fd9
Source dataset
uspto-grants-2007_03
Patent number
US07189741B2

Reaction notes

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