Acetic Acid → (R)-N-[2-(4-Methoxybenzoylamino)-2-phenylethyl]-1-isopropylpiperidine-4-carboxamide

HRID 23957Notes

Reaction equation

HRID 23957 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:35]=[CH:34][C:13]([C:14]([NH:16][C@H:17]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:18][NH:19][C:20]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[O:21])=[O:15])=[CH:12][CH:11]=1.[CH3:36][C:37]([CH3:39])=O.C(O)(=O)C.C([BH3-])#N.[Na+].[NH4+].[OH-]>CO.C(Cl)Cl>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:16][C@H:17]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:18][NH:19][C:20]([CH:22]2[CH2:27][CH2:26][N:25]([CH:37]([CH3:39])[CH3:36])[CH2:24][CH2:23]2)=[O:21])=[O:15])=[CH:34][CH:35]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 180AcetoneHCID 14923Ammonium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 69592699(R)-N-[2-(4-Methoxybenzoylamino)-2-phenylethyl]piperidine-4-carboxamide trifluoroacetate

Product 1

HCID 54102863(R)-N-[2-(4-Methoxybenzoylamino)-2-phenylethyl]-1-isopropylpiperidine-4-carboxamideYield 70.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 6344DichloromethaneSolvent

Procedure

(Alkylation Method A) (R)-N-[2-(4-Methoxybenzoylamino)-2-phenylethyl]piperidine-4-carboxamide trifluoroacetate (0.50 g, 1.0 mmol), acetone (4.5 mL, 61 mmol), acetic acid (0.28 mL, 4.9 mmol), and sodium cyanoborohydride (0.32 g, 5.1 mmol) were combined in methanol, and stirred. After 4 h, TLC (79% CH2Cl2, 19% methanol, 1% NH4OH) indicated reaction completion. The solution was diluted with methanol (100 mL), and passed through H+ form ion exchange resin (Varian SCX cartridge, Catalog #1225-6035) washed with methanol, and then with 2 M NH3 in methanol to collect the product. The product was recrystallized from methanol and ether to afford 0.30 g (70%) of a white crystalline solid

Workup

  1. customreaction completion
  2. customform ion exchange resin (Varian SCX cartridge, Catalog #1225-6035)
  3. washwashed with methanol
  4. customwith 2 M NH3 in methanol to collect the product
  5. customThe product was recrystallized from methanol and ether

Sources & evidence

ORD record
ord-0355da86d87b4cc396e86117d3587e5e
Source dataset
uspto-grants-2005_02
Patent number
US06855715B1

Reaction notes

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