Triethylamine → Phenol, 4-[4-[4-(trifluoroMethoxy)phenoxy]-1-piperidinyl]-, 4-Methylbenzenesulfonate (salt)

HRID 2354030Notes

Reaction equation

HRID 2354030 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.O.[C:35]1([CH3:45])[CH:40]=[CH:39][C:38]([S:41]([OH:44])(=[O:43])=[O:42])=[CH:37][CH:36]=1>C(O)C>[C:35]1([CH3:45])[CH:36]=[CH:37][C:38]([S:41]([OH:44])(=[O:42])=[O:43])=[CH:39][CH:40]=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 8471TriethylamineHCID 125111,4-CyclohexanedioneHCID 521998p-Toluenesulfonic acid monohydrateHCID 161154394-[4-(Trifluoromethoxy)phenoxy]piperidine

Product 1

HCID 86615244Phenol, 4-[4-[4-(trifluoroMethoxy)phenoxy]-1-piperidinyl]-, 4-Methylbenzenesulfonate (salt)Yield 63.75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.00 g of 4-(4-trifluoromethoxyphenoxy)piperidine, 2.575 g of 1,4-cyclohexanedione and 2.16 ml of triethylamine were heated in 60 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 4.37 g of p-toluenesulfonic acid monohydrate was added. After leaving at room temperature for 30 minutes, the precipitate was filtrated, washed with ethyl acetate and air-dried, and 5.116 g of 1-(4-hydroxyphenyl)-4-(4-trifluoromethoxyphenoxy)piperidine p-toluenesulfonate was obtained (yield 63.75%).

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. customair-dried

Sources & evidence

ORD record
ord-a461e8d53b7c49258e679463feb20bd6
Source dataset
uspto-grants-2010_07
Patent number
US07750156B2

Reaction notes

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