(4-Fluorobenzyl)triphenylphosphonium chloride → HCID 68831952, compound

HRID 1786510Notes

Reaction equation

HRID 1786510 reaction equation
[Cl-:1].[F:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.[K].C([O-])(C)(C)C.[CH3:35][N:36]([CH3:51])[C:37]1([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH2:42][CH2:41][CH:40]([CH:43]=O)[CH2:39][CH2:38]1>C1COCC1>[ClH:1].[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[CH:43][CH:40]2[CH2:39][CH2:38][C:37]([N:36]([CH3:35])[CH3:51])([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH2:42][CH2:41]2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 2733554(4-Fluorobenzyl)triphenylphosphonium chlorideHCID 104439064-Dimethylamino-4-phenylcyclohexanecarbaldehydeHCID 50987170Potassium tertbutoxide

Product 1

HCID 68831952HCID 68831952, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

4-fluorobenzyltriphenyl phosphonium chloride (1.22 g, 3 mmole) was suspended under argon in abs. THF (15 ml) and cooled to −5° C. Potassium-tert-butanolate (337 mg, 3 mmole) dissolved in THF (14 ml) was added dropwise and the mixture post-stirred for 30 min at <0°. 4-dimethylamino-4-phenylcyclohexane carbaldehyde (467 mg, 2 mmole) dissolved in THF (8 ml) was subsequently added dropwise and the mixture stirred for 20 h with gradual heating to RT. For working up, the mixture was evaporated and 15 ml 1M HCl, 5 ml water and 30 ml ether were added to the residue. After stirring for 60 min, between the aqueous phase and the organic phase, there was a white solid which was suction filtered and washed with ether (3×2 ml). Following analysis and DC, this solid was the hydrochloride of the least polar of four possible diastereoisomers of {4-[2-(4-fluorophenyl)vinyl]-1-phenylcyclohexyl}dimethylamine (145 mg, mp. 255 to 258° C.).

Workup

  1. additionwas added dropwise
  2. additionwas subsequently added dropwise
  3. stirringthe mixture stirred for 20 h
  4. customthe mixture was evaporated
  5. addition15 ml 1M HCl, 5 ml water and 30 ml ether were added to the residue
  6. stirringAfter stirring for 60 min, between the aqueous phase
  7. filtrationfiltered
  8. washwashed with ether (3×2 ml)

Sources & evidence

ORD record
ord-fbec5948a29a4f66ba74d90f261126e9
Source dataset
uspto-grants-2009_03
Patent number
US07507758B2

Reaction notes

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