Sodium Hydroxide → HCID 68883740, compound

HRID 1986042Notes

Reaction equation

HRID 1986042 reaction equation
C(N1C=CN=C1)([N:3]1[CH:7]=[CH:6]N=C1)=O.[CH3:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([OH:26])=O)=[CH:19][CH:18]=1)(=[O:16])=[O:15].[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][CH:37](CCN)[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].[OH-].[Na+]>C1COCC1.C1(C)C=CC=CC=1>[C:27]([O:31][C:32]([N:34]1[CH2:35][CH2:36][CH:37]([N:3]([CH2:7][CH3:6])[C:24](=[O:26])[CH2:23][C:20]2[CH:19]=[CH:18][C:17]([S:14]([CH3:13])(=[O:15])=[O:16])=[CH:22][CH:21]=2)[CH2:38][CH2:39]1)=[O:33])([CH3:28])([CH3:29])[CH3:30]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 682631,1'-Carbonyldiimidazole2×HCID 5723454-Mesylphenylacetic acidHCID 1514258tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylate

Product 1

HCID 68883740HCID 68883740, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A slurry of carbonyldiimidazole (1.94 g, 11.98 mmol) in THF (10 ml) was treated with a solution of 4-methylsulphonylphenylacetic acid (2.5 g, 11.68 mmol) in THF (12.5 ml) at ambient temperature and then heated to 50° C. After one hour carbonyldiimidazole (0.189 g, 1.17 mmol) was added. After a further 15 minutes a solution of N-(1-tert-butoxycarbonyl-4-piperidinyl)ethylamine (2.53 g, 11.10 mmol) in toluene (10 ml) was added dropwise over two minutes to the reaction mixture. After 30 minutes at 50° C. the reaction mixture was treated with 1M NaOH (12.5 ml) and the mixture was stired rapidly for 30 min and then allowed to cool to room temperature. The organic layer was separated and washed with aqueous citric acid (10% w/w, 10 ml) and then with water (5 ml). The organic layer was evaporated to dryness to afford N-(1-tert-butoxycarbonyl-4-piperidinyl)-N-ethyl-4-methanesulfonylphenyl-acetamide as a colourless oil (4.75 g, 100%).

Workup

  1. temperatureto cool to room temperature
  2. customThe organic layer was separated
  3. washwashed with aqueous citric acid (10% w/w, 10 ml)
  4. customThe organic layer was evaporated to dryness

Sources & evidence

ORD record
ord-1cc6c5f85c4d49a0b2feb9cebfd72209
Source dataset
uspto-grants-2009_06
Patent number
US07547789B2

Reaction notes

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