Hydrochloric Acid → HCID 67233469, compound

HRID 2047435Notes

Reaction equation

HRID 2047435 reaction equation
[CH2:1]([N:8]1[CH2:13][C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[C:11]([C:21]([O:23]CC)=[O:22])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:26]>C(O)(=O)C>[ClH:26].[CH2:1]([N:8]1[CH2:13][C:12]([C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)=[C:11]([C:21]([OH:23])=[O:22])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67231905HCID 67231905, compound

Product 1

HCID 67233469HCID 67233469, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To the compound (11.1 g) obtained in step 1 were added acetic acid (25 mL) and hydrochloric acid (25 mL), and the mixture was heated at 100° C. for 2 hr. The reaction mixture was cooled and concentrated to give 1-benzyl-5-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine-4-carboxylic acid monohydrochloride (8.82 g, 78%). 1H-NMR (DMSO-d6): δ 2.70-2.80 (2H, m), 3.10-3.60 (2H, m), 3.85-4.00 (2H, m), 4.30-4.50 (2H, m), 7.18-7.25 (4H, m), 7.42-7.48 (3H, m), 7.62-7.68 (2H, m), 11.3-11.5 (1H, brs), 12.4-13.0 (1H, br)

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-74bd1394c84b4e56b8322b0678b737dd
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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