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

HRID 395816Notes

Reaction equation

HRID 395816 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-42475e6d16ee4ec4af2161468ebb36f9
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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