Potassium Carbonate → HCID 86709374, compound

HRID 2172191Notes

Reaction equation

HRID 2172191 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([CH:28]=O)=[CH:24][CH:23]=2)=[CH:18][CH:17]=1.[F:30][C:31]([F:47])([F:46])[O:32][C:33]1[CH:45]=[CH:44][C:36]([O:37][CH:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[F:47][C:31]([F:30])([F:46])[O:32][C:33]1[CH:45]=[CH:44][C:36]([O:37][CH:38]2[CH2:39][CH2:40][N:41]([CH2:28][C:25]3[CH:24]=[CH:23][C:22]([C:19]4[CH:18]=[CH:17][C:16]([OH:15])=[CH:21][CH:20]=4)=[CH:27][CH:26]=3)[CH2:42][CH2:43]2)=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 27592994-(4-hydroxyphenyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 161154394-[4-(Trifluoromethoxy)phenoxy]piperidine

Product 1

HCID 86709374HCID 86709374, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (1.69 g) was added to a 1,2-dichloroethane solution (11 ml) of 4′-hydroxybiphenyl-4-carbaldehyde (1.13 g) and 4-(4-trifluoromethoxyphenoxy)piperidine (1.78 g) and stirred at room temperature overnight. A potassium carbonate aqueous solution was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→0:10) to afford the title compound as a yellow powder (1.73 g).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→0:10)

Sources & evidence

ORD record
ord-4142d366029a4c22b1943b3f75290232
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

Loading…