1-Hydroxybenzotriazole → 2-(2,2-Dimethoxy-ethyl)-6-(4-phenyl-butylcarbamoyl)-piperidine-1-carboxylic Acid Benzyl Ester

HRID 987096Notes

Reaction equation

HRID 987096 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:16]([CH2:17][CH:18]([O:21][CH3:22])[O:19][CH3:20])[CH2:15][CH2:14][CH2:13][CH:12]1[C:23](O)=[O:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]1([CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH:12]([C:23](=[O:24])[NH:36][CH2:35][CH2:34][CH2:33][CH2:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:17][CH:18]([O:21][CH3:22])[O:19][CH3:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 83242BenzenebutanamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 543519096-(2,2-Dimethoxy-ethyl)-piperidine-1,2-dicarboxylic acid 1-benzyl ester2×

Product 1

HCID 543007762-(2,2-Dimethoxy-ethyl)-6-(4-phenyl-butylcarbamoyl)-piperidine-1-carboxylic Acid Benzyl EsterYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(2,2-Dimethoxy-ethyl)-piperidine-1,2-dicarboxylic acid 1-benzyl ester (Compound 238, 1 g, 2.85 mmol) and 4-phenylbutyl amine (0.51 g, 3.42 mmol) were dissolved in CH2Cl2 (60 mL). HOBt (0.462 g, 3.42 mmol) was added followed by EDC.HCl (0.655 g, 3.42 mmol). The reaction was stirred at room temperature for 12 hours. Saturated NaHCO3 (25 mL) was added and the reaction was extracted with CHCl3 (2×50 mL). The combined organic layers were dried over Na2SO4, and then concentrated. Flash chromatographic purification of the residue (1:1 EtOAc/hexanes) gave Compound 242 (1.294 g, 94%). Rf=0.62 (1:1 EtOAC/hexanes).

Workup

  1. extractionthe reaction was extracted with CHCl3 (2×50 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customFlash chromatographic purification of the residue (1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-f69428103cba4ea5a64bd5fec716da3e
Source dataset
uspto-grants-2003_10
Patent number
US06630472B1

Reaction notes

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