Ethyl 4-piperidinecarboxylate → HCID 86626750, compound

HRID 603989Notes

Reaction equation

HRID 603989 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:6][N:7]([C:26]1[N:31]=[CH:30][C:29](Br)=[CH:28][N:27]=1)[CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[N:19]([CH2:24][CH3:25])[CH2:20][CH2:21][O:22][CH3:23].CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[NH:69]1[CH2:74][CH2:73][CH:72]([C:75]([O:77][CH2:78][CH3:79])=[O:76])[CH2:71][CH2:70]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cl-].[Na+].O>[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:6][N:7]([CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[N:19]([CH2:24][CH3:25])[CH2:20][CH2:21][O:22][CH3:23])[C:26]1[N:31]=[CH:30][C:29]([N:69]2[CH2:74][CH2:73][CH:72]([C:75]([O:77][CH2:78][CH3:79])=[O:76])[CH2:71][CH2:70]2)=[CH:28][N:27]=1

Participants

8

Reactant 4

HCID 70770Ethyl 4-piperidinecarboxylateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 86626749HCID 86626749, compound

Product 1

HCID 86626750HCID 86626750, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 9811564Bis(dibenzylideneacetone)palladiumSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(3,5-Bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-{2-[ethyl-(2-methoxy-ethyl)-amino]-5-trifluoromethyl-benzyl}-amine (350 mg) is dissolved in toluene (5 ml) and tris(dibenzylideneacetone)dipalladium (49 mg), sodium tert-butoxide (77 mg), 2-(di-tert-butylphosphino)biphenyl (63 mg) and ethyl piperidine-4-carboxylate (119 μl) and the mixture is stirred under nitrogen flow at room temperature overnight. To the reaction solution is added a saturated brine, and the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane ethyl acetate=19:1→3:1) to give ethyl 1-[2-((3,5-bis-trifluoromethyl-benzyl)-{2-[ethyl-(2-methoxy-ethyl)-amino]-5-trifluoromethyl-benzyl}amino)-pyrimidin-5-yl]-piperidine-4-carboxylate (212 mg). MS (m/z): 7:36 [M+H]+

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (hexane ethyl acetate=19:1→3:1)

Sources & evidence

ORD record
ord-27fc1004c4d042089337dc3081bd3e11
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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