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

HRID 1182071Notes

Reaction equation

HRID 1182071 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-5da2efb6be014092b78ce61c208c336e
Source dataset
uspto-grants-2007_10
Patent number
US07288540B2

Reaction notes

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