1,2-Dichloroethane → HCID 69158729, compound

HRID 967391Notes

Reaction equation

HRID 967391 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[CH2:22][CH2:23][C:24](O)=[O:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:15]3[C:16](=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=3)[CH2:22][CH2:23][C:24]2=[O:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 111,2-DichloroethaneHCID 69156675HCID 69156675, compound

Product 1

HCID 69158729HCID 69158729, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-[2-(2-Carboxy-ethyl)-4-chloro-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester (3.9 g, 10.1 mmol) and EDC (2.9 g, 15.3 mmol) were set stirring in CH2Cl2 (50 mL) for 2 h. The reaction mixture was dissolved in CH2Cl2 (150 mL), washed with water (2×50 mL) and brine (1×50 mL). The organic layer was dried over Na2SO4 and concentrated. The residue was purified by column chromatography (silica, 30-50% EtOAc/hexanes) to obtain 1.9 g (52%) of the desired product. TLC (silica, 50% EtOAc/hexanes): Rf=0.67. MS (electrospray): exact mass calculated for C19H25ClN2O3, 364.16. m/z found, 365.1 [M++H]. 1H NMR (400 MHz, CDCl3): 7.14-7.08 (m, 2H), 6.98 (d, J=8.61 Hz, 1H), 4.33-3.98 (m, 3H), 2.75 (t, J=7.83 Hz, 4H), 2.55-2.36 (m, 4H), 1.70-1.65 (m, 2H), 1.44 (s, 9H).

Workup

  1. washwashed with water (2×50 mL) and brine (1×50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (silica, 30-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6d39abd6ca5e423883f8573341a03038
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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