Trifluoroacetic acid → HCID 29006581, compound

HRID 351533Notes

Reaction equation

HRID 351533 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:17][CH:16]=2)(O)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[CH2:22]([O:21][C:18]1[CH:17]=[CH:16][C:15]([C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)=[CH:20][CH:19]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 22713211HCID 22713211, compound

Product 1

HCID 29006581HCID 29006581, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

To a solution of 1-tert-butoxycarbonyl-4-(4-hexyloxyphenyl)-4-hydroxypiperidine (6.856 g) in dichloromethane (34 ml) was added trifluoroacetic acid (17 ml) and stirred for 30 minutes at 4° C. The reaction mixture was adjusted to pH 12 with 2M aqueous NaOH. The organic layer was separated, washed with water and dried over magnesium sulfate and evaporated under reduced pressure to give 4-(4-hexyloxyphenyl)-1,2,3,6-tetrahydropiridine (3.59 g)

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-eafe026e7be54b258f75d2a329ae12ab
Source dataset
uspto-grants-2004_06
Patent number
US06743776B2

Reaction notes

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