Piperidine → 1-[(4-Bromophenyl)methyl]piperidine

HRID 1455174Notes

Reaction equation

HRID 1455174 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(O)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 707414-BromobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 164950451-[(4-Bromophenyl)methyl]piperidine

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

A solution of 4-bromobenzaldehyde (5 g), piperidine (2.9 mL), and acetic acid (1.5 mL) in DCE (65 mL) was treated with sodium triacetoxyborohydride (6.9 g). After 27 h, the resulting mixture was treated with saturated aqueous sodium bicarbonate (50 mL), and extracted with DCM (2×50 mL). The combined organic phases were dried (magnesium sulfate) and evaporated. Kugelrohr distillation of the residue (160° C., 5 mm Hg) gave the title compound as a pale yellow oil (5.9 g).

Workup

  1. extractionextracted with DCM (2×50 mL)
  2. dry with materialThe combined organic phases were dried (magnesium sulfate)
  3. customevaporated
  4. distillationKugelrohr distillation of the residue (160° C., 5 mm Hg)

Sources & evidence

ORD record
ord-3d2f066ae78c4e5f9f73ff58cffaf0a5
Source dataset
uspto-grants-2009_01
Patent number
US07482364B2

Reaction notes

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