Triethylamine → 2-(4-Benzyl-4-hydroxy-piperidin-1-yl)-N-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl)-acetamide

HRID 1419920Notes

Reaction equation

HRID 1419920 reaction equation
[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:17])[CH2:15]Cl)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:27]([C:34]1([OH:40])[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C=O>[CH2:27]([C:34]1([OH:40])[CH2:39][CH2:38][N:37]([CH2:15][C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:19])[CH3:18])=[CH:8][CH:9]=2)=[O:17])[CH2:36][CH2:35]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 981524-Benzyl-4-piperidinolHCID 70046914N-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-chloro-acetamide

Product 1

HCID 700460592-(4-Benzyl-4-hydroxy-piperidin-1-yl)-N-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl)-acetamideYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-chloro-acetamide (1.14 g, 3.8 mmol) was dissolved in dimethylformamide (DMF) (12 ml) and stirred for 19 hours at room temperature in the presence of triethylamine (0.79 ml, 5.7 mmol) and 4-benzyl-4-hydroxypiperidin (0.87 g, 4.56 mmol). The reaction mixture was concentrated, dissolved in CH2Cl2 and washed with H2O (2×30 ml). The organic phase was dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexane-ethyl acetate 1:1 then ethyl acetate) to provide 2-(4-Benzyl-4-hydroxy-piperidin-1-yl)-N-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-acetamide (1.32 g, 78%) as a yellow solid, m.p. 105°-108° C. and MS: m/e=455.5 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in CH2Cl2
  3. washwashed with H2O (2×30 ml)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed over silica gel (hexane-ethyl acetate 1:1

Sources & evidence

ORD record
ord-7c9ff282444740618e1bde4995878586
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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