7-chloro-3-(1-tert-butoxycarbonylpiperidin-4-yl)-1H-indole → 7-chloro-3-(piperidin-4-yl)-1H-indole

HRID 586726Notes

Reaction equation

HRID 586726 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[C:18]([Cl:23])[CH:19]=[CH:20][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:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:17]=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 120720357-chloro-3-(1-tert-butoxycarbonylpiperidin-4-yl)-1H-indoleHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 120720367-chloro-3-(piperidin-4-yl)-1H-indoleYield 146.2%

Procedure

4-(7-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. 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-e0c6f17508554fadbb16970dd0e1b516
Source dataset
uspto-grants-2005_08
Patent number
US06936603B2

Reaction notes

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