Phenethylamine → 2-(2,2-Dimethoxy-ethyl)-6-phenethylcarbamoyl-piperidine-1-carboxylic Acid Benzyl Ester

HRID 987094Notes

Reaction equation

HRID 987094 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.[CH2:26]([NH2:34])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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:34][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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 1001PhenethylamineHCID 757711-HydroxybenzotriazoleHCID 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 545104932-(2,2-Dimethoxy-ethyl)-6-phenethylcarbamoyl-piperidine-1-carboxylic Acid Benzyl EsterYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(2,2-Dimethoxy-ethyl)-piperidine-1,2-dicarboxylic acid 1-benzyl ester (Compound 238, 0.335 g, 0.96 mmol) and phenethyl amine (0.14 g, 1.15 mmol) were dissolved CH2Cl2 (20 mL). HOBt (0.156 g, 1.15 mmol) was added followed by EDC.HCl (0.221 g, 1.15 mmol). The reaction was stirred at room temperature for 18 hours. Saturated NaHCO3 solution (25 mL) was added and then 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 239 (0.374 g, 86%). Rf=0.47 (1:1 EtOAC/hexanes).

Workup

  1. extractionextracted 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-dca6f6e4208b4f12b57989d2c6f8a457
Source dataset
uspto-grants-2003_10
Patent number
US06630472B1

Reaction notes

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