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

HRID 227268Notes

Reaction equation

HRID 227268 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 were 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 sulphate. 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 sulphate
  4. filtrationAfter filtration
  5. customthe solvent was removed under reduced pressure
  6. customaffording

Sources & evidence

ORD record
ord-8e3468f08205490c909d4ea8817fc8d3
Source dataset
uspto-grants-2009_07
Patent number
US07560471B2

Reaction notes

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