Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate → HCID 11974826, compound

HRID 1373323Notes

Reaction equation

HRID 1373323 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[Cl:16][C:17]1[C:22]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3F)[N:27]=[CH:26][N:25]=2)=[C:21]2[O:35][CH2:36][O:37][C:20]2=[CH:19][CH:18]=1>Cl.C(OCC)C>[ClH:16].[ClH:16].[Cl:16][C:17]1[C:22]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3[O:15][CH2:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[N:27]=[CH:26][N:25]=2)=[C:21]2[O:35][CH2:36][O:37][C:20]2=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 11974447HCID 11974447, compound

Product 1

HCID 11974826HCID 11974826, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

Using an analogous procedure to that described in Example 37, N-(tert-butoxycarbonyl)piperidin-4-ylmethanol was reacted with 4-(6-chloro-2,3-methylenedioxyanilino)-5-fluoroquinazoline (0.1 g). The product so obtained was dissolved in a 2M solution of hydrogen chloride in diethyl ether (20 ml) and stirred at ambient temperature for 3 hours. The mixture was evaporated and the residue was triturated under diethyl ether. The solid so obtained was washed with diethyl ether and dried under vacuum. There was thus obtained the title compound (0.121 g); NMR Spectrum: (DMSOd6) 1.5–1.6 (m, 2H), 1.9–2.0 (m, 2H), 2.3–2.4 (m, 1H), 2.8–2.9 (m, 2H), 3.3 (d, 2H), 4.42 (d, 2H), 6.15 (s, 2H), 7.07 (d, 1H), 7.15 (d, 1H), 7.53 (m, 2H), 8.06 (m, 1H), 8.87 (s, 1H), 10.57 (br s, 1H); Mass Spectrum: M+H+ 413 and 415.

Workup

  1. customThe product so obtained
  2. customThe mixture was evaporated
  3. customthe residue was triturated under diethyl ether
  4. customThe solid so obtained
  5. washwas washed with diethyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-421314fd98de4a2e95e7ebf1990bb711
Source dataset
uspto-grants-2007_01
Patent number
US07160891B2

Reaction notes

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