4-(5-fluoro-1H-indole-2-carbonyl)-4-propyl-piperidine-1-carboxylic acid tert-butyl ester → (5-fluoro-1H-indol-2-yl)-(4-propyl-piperidin-4-yl)-methanone

HRID 661570Notes

Reaction equation

HRID 661570 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([F:28])=[CH:23][CH:22]=3)=[O:18])([CH2:14][CH2:15][CH3:16])[CH2:10][CH2:9]1)=O)(C)(C)C>Cl>[F:28][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19]([C:17]([C:11]1([CH2:14][CH2:15][CH3:16])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:18])=[CH:27]2

Participants

3

Reactant 1

HCID 666875844-(5-fluoro-1H-indole-2-carbonyl)-4-propyl-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 56932306(5-fluoro-1H-indol-2-yl)-(4-propyl-piperidin-4-yl)-methanoneYield 97%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-(5-fluoro-1H-indole-2-carbonyl)-4-propyl-piperidine-1-carboxylic acid tert-butyl ester 162 mg was dissolved in 1 M methanolic HCl and stirred at room temperature for 24 hours. The solvent was removed to afford an oil which was precipitated from diethyl ether to give (5-fluoro-1H-indol-2-yl)-(4-propyl-piperidin-4-yl)-methanone; hydrochloride 132 mg as a solid in 97% yield, MS=289 [M+H]+.

Workup

  1. customThe solvent was removed
  2. customto afford an oil which
  3. customwas precipitated from diethyl ether

Sources & evidence

ORD record
ord-f85a544adf0448b786950c8c45b1812e
Source dataset
uspto-grants-2011_12
Patent number
US08084623B2

Reaction notes

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