Potassium Carbonate → 4-{Bis[4-(trifluoromethyl)phenyl]methylene}-1-[(4-nitrophenyl)methyl]piperidine

HRID 1594336Notes

Reaction equation

HRID 1594336 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[C:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1.[N+:28]([C:31]1[CH:36]=[CH:35][C:34]([CH2:37]Br)=[CH:33][CH:32]=1)([O-:30])=[O:29].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[F:24][C:22]([F:25])([F:23])[C:19]1[CH:20]=[CH:21][C:16]([C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:26])[F:27])=[CH:8][CH:7]=2)=[C:10]2[CH2:15][CH2:14][N:13]([CH2:37][C:34]3[CH:35]=[CH:36][C:31]([N+:28]([O-:30])=[O:29])=[CH:32][CH:33]=3)[CH2:12][CH2:11]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 660114-Nitrobenzyl bromide2×HCID 85981203HCID 85981203, compound

Product 1

HCID 866055684-{Bis[4-(trifluoromethyl)phenyl]methylene}-1-[(4-nitrophenyl)methyl]piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A stirred mixture of 3.8 grams (0.010 mole) of 4-{bis[4-(trifluoromethyl)phenyl]methylene}piperidine, 2.2 grams (0.010 mole) of 4-nitrophenylmethyl bromide, and 1.7 grams (0.012 mole) of potassium carbonate in about 20 mL of ethanol was warmed to 75° C., where it stirred for about 18 hours. After this time, an additional 0.2 gram (0.001 mole) of 4-nitrophenylmethyl bromide and an additional 0.2 gram (0.001 mole) of potassium carbonate was added to the reaction mixture. The reaction mixture was again heated to 75° C., where it stirred for about eight hours. After this time, the reaction mixture was cooled and filtered to remove excess potassium carbonate. The reaction mixture was then taken up in acetic acid, and 0.2 gram (catalyst) of 5% platinum on carbon was added to the mixture in preparation for the following hydrogenation step. A quantitative yield of the subject compound was assumed.

Workup

  1. temperatureThe reaction mixture was again heated to 75° C.
  2. stirringwhere it stirred for about eight hours
  3. temperatureAfter this time, the reaction mixture was cooled
  4. filtrationfiltered
  5. customto remove excess potassium carbonate
  6. addition0.2 gram (catalyst) of 5% platinum on carbon was added to the mixture in preparation for the following hydrogenation step

Sources & evidence

ORD record
ord-64ad189837774151977203f47abbc7f9
Source dataset
uspto-grants-2007_11
Patent number
US07300946B2

Reaction notes

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