Piperidine → N-{4-[(Piperidin-1-yl)methyl]phenyl}acetamide

HRID 1777740Notes

Reaction equation

HRID 1777740 reaction equation
[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:13]1([CH2:9][C:8]2[CH:11]=[CH:12][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 5

HCID 8082PiperidineHCID 739424-AcetamidobenzaldehydeHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 348702N-{4-[(Piperidin-1-yl)methyl]phenyl}acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-acetamidobenzaldehyde (200 mg), piperidine (0.121 mL), NaBH(OAc)3 (636 mg) and DIPEA (0.617 mL) in DCM (4 mL) was stirred at RT for 4 h. DCM and sat. NaHCO3 were added. The phases were separated, the org. layer was dried (Na2SO4), filtered off and evaporated to dryness to afford 267 mg of white solid. LC-MS (B): tR=0.45 min; [M+H]+: 233.24.

Workup

  1. customThe phases were separated
  2. dry with materiallayer was dried (Na2SO4)
  3. filtrationfiltered off
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-578e7e78ee1c4990a038e179fb0342cd
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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