Phosgene → 5-(tert-butyldimethylsilyloxy)-2-phthalimido-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]aniline

HRID 842389Notes

Reaction equation

HRID 842389 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:16]2[C:20](=[O:21])[C:19]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]3[C:17]2=[O:26])=[C:13]([CH:15]=1)[NH2:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:27](Cl)(Cl)=[O:28].[N:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][CH:40]([CH2:43][OH:44])[CH2:39][CH2:38]2)=[CH:33][CH:32]=1>C1(C)C=CC=CC=1.C(Cl)Cl.CCCCCC>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:16]2[C:17](=[O:26])[C:18]3=[CH:25][CH:24]=[CH:23][CH:22]=[C:19]3[C:20]2=[O:21])=[C:13]([CH:15]=1)[NH:14][C:27]([O:44][CH2:43][CH:40]1[CH2:39][CH2:38][N:37]([C:34]2[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=2)[CH2:42][CH2:41]1)=[O:28])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 6371PhosgeneHCID 11310048(1-(Pyridin-4-YL)piperidin-4-YL)methanolHCID 181744945-(Tert-butyldimethylsilyloxy)-2-phthalimidoaniline

Product 1

HCID 181745295-(tert-butyldimethylsilyloxy)-2-phthalimido-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]anilineYield 90%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A solution of 5-(tert-butyldimethylsilyloxy)-2-phthalimidoaniline (1.02 g, 2.77 mmol) in toluene (15 mL) was treated with a solution of 20% phosgene in toluene (2 mL) at reflux for 20 min. The volatile materials were removed in vacuo to give a tan solid, which was dissolved in dry methylene chloride (20 mL) and treated with 1-(4-pyridyl)piperidine-4-methanol (0.53 g, 2.77 mmol). The resulting suspension was stirred for 90 min then diluted with hexane. The mixture was allowed to stand overnight and the resulting precipitate collected by vacuum filtration and dried to yield 1.46 g (90%) of the title compound as a tan powder.

Workup

  1. temperatureat reflux for 20 min
  2. customThe volatile materials were removed in vacuo
  3. customto give a tan solid, which
  4. waitto stand overnight
  5. filtrationthe resulting precipitate collected by vacuum filtration
  6. customdried

Sources & evidence

ORD record
ord-0acbb8ff5c624ef08e87a912bafd0b0a
Source dataset
uspto-grants-2002_04
Patent number
US06372759B1

Reaction notes

Loading…