Trityl chloride → 3-(Trityl-amino)-piperidin-2-one

HRID 2212177Notes

Reaction equation

HRID 2212177 reaction equation
[C:1]1([C:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl.[NH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][NH:26][C:25]1=[O:30].C(N(CC)CC)C>O1CCCC1>[C:7]([NH:23][CH:24]1[CH2:29][CH2:28][CH2:27][NH:26][C:25]1=[O:30])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 219636913-Amino-piperidin-2-one dihydrochloride

Product 1

HCID 147292243-(Trityl-amino)-piperidin-2-oneYield 45.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add triphenylmethyl chloride (35.11 g, 126.0 mmol) to a suspension of 3-amino-piperidin-2-one dihydrochloride (21.42 g, 114.5 mmol) in tetrahydrofuran (250 mL), follow by dropwise addition of triethylamine (55.9 mL, 400.8 mmol). Stir the reaction at room temperature under nitrogen overnight. Filter the mixture, wash with tetrahydrofuran, concentrate the filtrate to a yellow oil, and partition the material between 20% isopropanol/chloroform and water. Wash the organic layer with saturated aqueous sodium bicarbonate solution, brine, dry over magnesium sulfate and concentrate. Purify by flash chromatography on silica gel (eluting with 0–1.25% methanol/chloroform) which gives 18.50 g of the title compound as a white foam, 45% yield. 1H NMR: consistent with structure. MS (ion spray) 113 (M+−1).

Workup

  1. customthe reaction at room temperature under nitrogen overnight
  2. filtrationFilter the mixture
  3. washwash with tetrahydrofuran
  4. concentrationconcentrate the filtrate to a yellow oil
  5. custompartition the material between 20% isopropanol/chloroform and water
  6. washWash the organic layer with saturated aqueous sodium bicarbonate solution, brine
  7. dry with materialdry over magnesium sulfate
  8. concentrationconcentrate
  9. customPurify by flash chromatography on silica gel (eluting with 0–1.25% methanol/chloroform) which

Sources & evidence

ORD record
ord-0e948a608d7d414db116f88fd9c6ca3f
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

Loading…