Trifluoroacetic acid methylene chloride → HCID 22293778, compound

HRID 967400Notes

Reaction equation

HRID 967400 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=3)[CH2:16][C:15]2=[O:24])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[Cl:23][C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[N:14]([CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[C:15](=[O:24])[CH2:16]2

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 69158017HCID 69158017, compound

Product 1

HCID 22293778HCID 22293778, compoundYield 139.8%

Procedure

4-(5-Chloro-2-oxo-2,3-dihydro-indol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (3.4 g, 9.7 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 3.4 g (97%) of a white solid. MS (electrospray): exact mass calculated for C13H15ClN2O, 250.09. m/z found, 251.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6); 7.45 (s, 2H), 7.31 (d, J=8.1 Hz, 1H), 4.55-4.45 (m, 1H), 3.68 (s, 2H), 3.50 (d, J=12.3, 2H), 3.14 (m, 2H), 2.70-2.55 (m, 2H), 1.87 (d, J=13.1 Hz, 2H).

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-351412ef18d14dc19035c3864543cf0e
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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