Benzaldehyde → Benzyl({2-[4-(4-fluorophenyl)oxan-4-yl]ethyl})amine

HRID 76217Notes

Reaction equation

HRID 76217 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][CH2:15][NH2:16])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[CH2:17]([NH:16][CH2:15][CH2:14][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 68314438HCID 68314438, compound

Product 1

HCID 68314456Benzyl({2-[4-(4-fluorophenyl)oxan-4-yl]ethyl})amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(4-fluorophenyl)oxan-4-yl]ethan-1-amine (250 mg, 1.12 mmol) in anhydrous CH2Cl2 (5 ml) and NA2SO4 (159 mg, 1.12 mmol) at rt was added benzaldehyde (0.17 ml, 1.68 mmol). The reaction was stirred overnight. The reaction mixture was filtered and concentrated. The residue was dissolved in 5 ml MeOH at 0° C. and NaBH4 added in one portion (51 mg, 1.34 mmol). The reaction was stirred at 0° C. for 1 h. The solution was then quenched with H2O (10 ml), extracted with CH2Cl2 (3×20 ml), washed with brine (10 ml) and dried over NA2SO4. Purified by normal phase SiO2 chromatography (0 to 10% MeOH/CH2Cl2) to give benzyl({2-[4-(4-fluorophenyl) oxan-4-yl]ethyl})amine as a colorless oil (200 mg, 60%, m/z: 314.2 [M+H]+ observed).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 5 ml MeOH at 0° C.
  4. additionNaBH4 added in one portion (51 mg, 1.34 mmol)
  5. stirringThe reaction was stirred at 0° C. for 1 h
  6. customThe solution was then quenched with H2O (10 ml)
  7. extractionextracted with CH2Cl2 (3×20 ml)
  8. washwashed with brine (10 ml)
  9. customdried over NA2SO4
  10. customPurified by normal phase SiO2 chromatography (0 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-badf241c33f44666bbd223fe295d6b54
Source dataset
uspto-grants-2014_09
Patent number
US08835488B2

Reaction notes

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