p-Toluenesulfonic acid → Phenol, 4-[4-[4-(trifluoroMethoxy)phenoxy]-1-piperidinyl]-, 4-Methylbenzenesulfonate (salt)

HRID 2354029Notes

Reaction equation

HRID 2354029 reaction equation
[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1.[C:19]1(=O)[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1.C(N(CC)CC)C.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40]([OH:43])(=[O:42])=[O:41])=[CH:36][CH:35]=1>C(O)C>[C:34]1([CH3:44])[CH:35]=[CH:36][C:37]([S:40]([OH:43])(=[O:41])=[O:42])=[CH:38][CH:39]=1.[OH:25][C:22]1[CH:23]=[CH:24][C:19]([N:12]2[CH2:11][CH2:10][CH:9]([O:8][C:7]3[CH:15]=[CH:16][C:4]([O:3][C:2]([F:1])([F:17])[F:18])=[CH:5][CH:6]=3)[CH2:14][CH2:13]2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 125111,4-CyclohexanedioneHCID 161154394-[4-(Trifluoromethoxy)phenoxy]piperidine

Product 1

HCID 86615244Phenol, 4-[4-[4-(trifluoroMethoxy)phenoxy]-1-piperidinyl]-, 4-Methylbenzenesulfonate (salt)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

100 mg of 4-(4-trifluoromethoxyphenoxy)piperidine, 64 mg of 1,4-cyclohexanedione and 0.02 ml of triethylamine were heated in 15 ml of ethanol and reacted at 50° C. to 60° C. for 6 hours. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure and ethyl acetate was added thereto to prepare an ethyl acetate solution, to which p-toluenesulfonic acid was added. After leaving at room temperature for 30 minutes, the precipitate was filtrated and washed with ethyl acetate. The obtained crystal was air-dried and 139 mg of 1-(4-hydroxyphenyl)-4-(4-trifluoromethoxyphenoxy)piperidine p-toluenesulfonate was obtained.

Workup

  1. customreacted at 50° C. to 60° C. for 6 hours
  2. customAfter the completion of the reaction
  3. concentrationthe reaction mixture was concentrated under reduced pressure and ethyl acetate
  4. additionwas added
  5. customto prepare an ethyl acetate solution
  6. customAfter leaving at room temperature for 30 minutes
  7. filtrationthe precipitate was filtrated
  8. washwashed with ethyl acetate
  9. customThe obtained crystal was air-dried

Sources & evidence

ORD record
ord-8658746fbf204094ae690d4538a78d1e
Source dataset
uspto-grants-2010_07
Patent number
US07750156B2

Reaction notes

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