Benzaldehyde → 4-(1-Benzyl-piperidin-4-yloxy)-benzonitrile

HRID 459926Notes

Reaction equation

HRID 459926 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:17]([N:2]1[CH2:3][CH2:4][CH:5]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[CH2:6][CH2:7]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178322734-(Piperidin-4-yloxy)benzonitrile hydrochloride

Product 1

HCID 112663284-(1-Benzyl-piperidin-4-yloxy)-benzonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine 4-(piperidin-4-yloxy)-benzonitrile hydrochloride (64 mg, 0.268 mmol), benzaldehyde (55 μL, 0.536 mmol) and sodium triacetoxy borohydride (85 mg, 0.402 mmol) in CH2Cl2 (3 mL). Stir at room temperature overnight. Dilute the reaction mixture with CH2Cl2 (3 mL) and wash with NaOH (1M aq. 5 mL). Separate the organic layer and place it in an SCX column, eluting with ammonia (2.0M in methanol) to provide the title compound (74 mg, 95%).

Workup

  1. washwash with NaOH (1M aq. 5 mL)
  2. customSeparate the organic layer and place it in an SCX column
  3. washeluting with ammonia (2.0M in methanol)

Sources & evidence

ORD record
ord-3a0e7436286b4c1089f4e4737f0fef18
Source dataset
uspto-grants-2007_03
Patent number
US07196100B2

Reaction notes

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