Benzyl Bromide → HCID 18942180, compound

HRID 355392Notes

Reaction equation

HRID 355392 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH4-].[Na+]>CN(C)C=O.C(O)C>[CH2:16]([N:13]1[CH2:12][CH:11]=[C:10](/[CH:9]=[CH:8]/[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:15][CH2:14]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 4311764Sodium borohydrideHCID 5375544HCID 5375544, compound

Product 1

HCID 18942180HCID 18942180, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (E)-4-[2-(4-fluorophenyl)ethenyl]pyridine (18.75 g, 94.2 mmol) in dimethylformamide (30 ml) at 90° C. was added benzyl bromide (11.9 ml, 100 mmol) and the reaction stirred at 90° C. for 1 hour. The reaction was cooled to room temperature, diluted with ethanol (400 ml) and sodium borohydride (4 g, 105 mmol) added in portions. The reaction was stirred at room temperature for 2 hours, after which time the solvent was evaporated to a slurry. Methanol was added, and the resultant solid filtered and dried to yield (E)-1-benzyl-4-[2-(4-fluorophenyl)ethenyl]-1,2,3,6-tetrahydropyridine (12 g, 44%) as a white solid. δH (CDCl3) 2.41 (2H, br s, tetrahydropyridinyl CH2), 2.68 (2H, t, J 5.8 Hz, tetrahydropyridinyl CH2), 3.14 (2H, br s, tetrahydropyridinyl CH2), 3.63 (2H, s, NCH2Ar), 5.80 (1H, br s, tetrahydropyridinyl 5-CH), 6.40 (1H, d, J 16.2 Hz, ArCHCHC), 6.69 (2H, d, J 16.2 Hz, ArCHCHC), 6.96-7.02 (2H, m, ArH) and 7.25-7.39 (7H, m, ArH).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. additionadded in portions
  3. stirringThe reaction was stirred at room temperature for 2 hours
  4. customafter which time the solvent was evaporated to a slurry
  5. additionMethanol was added
  6. filtrationthe resultant solid filtered
  7. customdried

Sources & evidence

ORD record
ord-aa64dcc484104cf49d2bdc6f27d5a275
Source dataset
uspto-grants-1998_11
Patent number
US05830901

Reaction notes

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