tert-butyl 4-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylate → 4-(5-chloro-[1H]-indol-3-yl)-piperidine

HRID 497356Notes

Reaction equation

HRID 497356 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([Cl:23])[CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[Cl:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

3

Reactant 2

HCID 12072033tert-butyl 4-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylateHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 128313754-(5-chloro-[1H]-indol-3-yl)-piperidineYield 146.2%

Procedure

4-(5-Chloro-1H-indol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester (3.4 g, 10.2 mmol) was set stirring in 1:1 TFA/CH2Cl2. After 45 min the mixture was evaporated and the golden oil brought up in Et2O. A solid formed and was filtered, washed with Et2O and air dried to give 3.5 g (97%) of a white solid as a TFA salt. MS (electrospray): exact mass calculated for C12H15ClN2, 234.09; m/z found, 235.1 [M++H].

Workup

  1. customAfter 45 min the mixture was evaporated
  2. customA solid formed
  3. filtrationwas filtered
  4. washwashed with Et2O and air
  5. customdried

Sources & evidence

ORD record
ord-ec7b4605b11f4d08bee855488c8461c8
Source dataset
uspto-grants-2005_09
Patent number
US06949540B2

Reaction notes

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