Hydrochloric Acid → 4-(7-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperidine

HRID 1986944Notes

Reaction equation

[F:1][C:2]([F:22])([F:21])[C:3]1[C:8]2[S:9][CH:10]=[C:11]([CH:12]3[CH2:17][CH2:16][N:15](C(=O)C)[CH2:14][CH2:13]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[F:22][C:2]([F:1])([F:21])[C:3]1[C:8]2[S:9][CH:10]=[C:11]([CH:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-[4-(7-trifluoromethyl-benzo[b]thiophen-3-yl)-piperidin-1-yl]-ethanone (2.95 g, 9.01 mmol), concentrated HCl (30 mL), and ethanol was heated at 80° C. for 18 h. After cooling to room temperature, the reaction was basified with 20% aqueous potassium carbonate (150 mL) and the mixture extracted with DCM (2×100 mL). The organics were washed with water (100 mL), dried over potassium carbonate, filtered, and concentrated to give 2.42 g (94%) the desired product as an amber waxy solid.

Workup

temperatureAfter cooling to room temperature
extractionthe mixture extracted with DCM (2×100 mL)
washThe organics were washed with water (100 mL)
dry with materialdried over potassium carbonate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-3612c57d38ee4cf687bf4f8931a8f78b
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550469B2

Reaction notes

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