Hydrochloric Acid → HCID 69181929, compound

HRID 915110Notes

Reaction equation

HRID 915110 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:7]=2[C:6]=1[CH:15]1[CH2:20][CH2:19][N:18](C(=O)C)[CH2:17][CH2:16]1)=[O:4].[ClH:24]>CO>[ClH:24].[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:7]=2[C:6]=1[CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10314889HCID 10314889, compound

Product 1

HCID 69181929HCID 69181929, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 24.4 g (66.8 mmol) of 3-(1-acetyl-piperidin-4-yl)-6-fluoro-benzo[b]thiophene-2-carboxylic acid methyl ester in 400 mL of MeOH and 50 mL of concentrated HCl was heated a reflux for 2 days. When the solution was allowed to cool to room temperature the white precipitate was filtered, washed with methanol and dried to give 17.9 g (74%) of product as a white powder. MS (electrospray): exact mass calculated for C15H16FNO2S, 293.09; m/z found, 294.1 [M+H]+. 1H NMR (DMSO-d6, 400 MHz): 9.38 (br s, 1H), 9.02 (br s, 1H), 8.60 (dd, J=9.19, 5.09 Hz, 1H), 7.98 (dd, J=9.00, 2.54 Hz, 1H), 7.36 (dt, J=9.00, 2.54 Hz, 1H), 4.37 (br t, J=12.72 Hz, 1H), 3.87 (s, 3H), 3.40 (br d, J=11.93 Hz, 2H), 3.02 (q, J=11.35 Hz, 2H), 2.61 (dq, J=13.30, 3.72 Hz, 2H), 1.77 (br d, J=12.91 Hz, 2H).

Workup

  1. temperaturea reflux for 2 days
  2. filtrationwas filtered
  3. washwashed with methanol
  4. customdried

Sources & evidence

ORD record
ord-da3d87028723497bbbd1bf785f50cfed
Source dataset
uspto-grants-2007_09
Patent number
US07265102B2

Reaction notes

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