Benzene, 1-(chloromethyl)-2-fluoro- → 1-Benzyl-4-(2-fluorobenzyl)piperidin-4-ol

HRID 731532Notes

Reaction equation

HRID 731532 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[CH2:10]([N:17]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(OCC)C.C1COCC1.C(OCC)C>[CH2:10]([N:17]1[CH2:22][CH2:21][C:20]([CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[F:1])([OH:23])[CH2:19][CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 192201-Benzyl-4-piperidone

Product 1

HCID 127332241-Benzyl-4-(2-fluorobenzyl)piperidin-4-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21868444Ether tetrahydrofuranSolvent

Procedure

A suspension of Mg (3.50 g, 144 mmol) in diethyl ether (75 mL) was treated with 2-fluorobenzyl chloride (19.0 g, 131 mmol), stirred until all the Mg dissolved, treated with N-benzyl 4-piperidone (27.2 g, 144 mmol) in RATIO THF/diethyl ether (40 mL), and stirred at room temperature until the reaction was complete by TLC analysis. The mixture was partitioned between ethyl acetate and saturated NH4Cl and the aqueous layer was extracted with ethyl acetate twice. The combined organic layers were dried (MgSO4), filtered, and concentrated to give a residue which was used without further purification. MS (ESI) m/e 300 (M+H)+.

Workup

  1. dissolutiondissolved
  2. customThe mixture was partitioned between ethyl acetate and saturated NH4Cl
  3. extractionthe aqueous layer was extracted with ethyl acetate twice
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-a89df0c05632440984be306f0447ed74
Source dataset
uspto-grants-2009_09
Patent number
US07585858B2

Reaction notes

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