Hydrochloric Acid → HCID 23188865, compound

HRID 1728323Notes

Reaction equation

HRID 1728323 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[C:11]([OH:13])=O.[C:14]1([C:20]2([O:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[Na+].Cl>C1(C)C=CC=CC=1.O1CCCC1>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[C:11]([N:23]1[CH2:22][CH2:21][C:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([O:26][C:27]2[CH:28]=[CH:29][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:31][CH:32]=2)[CH2:25][CH2:24]1)=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 27236653,4-dihydro-2H-1-benzopyran-2-carboxylic acidHCID 212682524-Phenyl-4-(4-trifluoromethylphenoxy)piperidine

Product 1

HCID 23188865HCID 23188865, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.89 g (5.5 mmol) of 1,1-carbonyldiimidazole and 11 ml of dry tetrahydrofuran is added dropwise to a solution of 0.89 g (5.0 mmol) of 3,4-dihydro-2H-1-benzopyran-2-carboxylic acid and 5.5 ml of dry tetrahydrofuran at 20°-25° C. in the course of 1 hour. The reaction solution is then stirred at room temperature for a further 2 hours. A solution of 1.93 g (6.0 mmol) of 4-phenyl-4-(4-trifluoromethyl-phenoxy)-piperidine is then added dropwise at 25° C. in the course of 1 hour. After 18 hours at room temperature, the reaction solution is stirred into a mixture of 220 ml of 5% strength sodium chloride solution, 13 ml of 1 molar hydrochloric acid and 110 ml of toluene for working up. The aqueous phase is extracted once more with 55 ml of toluene. The combined organic phases are then washed with 55 ml each of 0.1 molar hydrochloric acid, followed by 1% strength sodium bicarbonate solution and then water. The organic phase is dried with sodium sulphate and concentrated to dryness.

Workup

  1. waitAfter 18 hours at room temperature
  2. extractionThe aqueous phase is extracted once more with 55 ml of toluene
  3. washThe combined organic phases are then washed with 55 ml each of 0.1 molar hydrochloric acid
  4. dry with materialThe organic phase is dried with sodium sulphate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9be23452aae0441c8e7d7a7ecf134392
Source dataset
uspto-grants-1994_07
Patent number
US05326771

Reaction notes

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