1,2-Dichloroethane → HCID 67264809, compound

HRID 1685117Notes

Reaction equation

HRID 1685117 reaction equation
[NH2:1][CH2:2][C@H:3]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7][CH2:6][N:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:4]1.[C:23](O)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(Cl)CCl.CCN(C(C)C)C(C)C>ClCCl>[C:23]([NH:1][CH2:2][C@H:3]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7][CH2:6][N:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:4]1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 57415720tert-Butyl (3R)-3-(aminomethyl)-4-benzylpiperazine-1-carboxylate

Product 1

HCID 67264809HCID 67264809, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a 50 mL round bottom flask was added 15S (820 mg, 2.68 mmol) and dichloromethane (15 mL). Benzoic acid (15T) (426 mg, 1.3 eq) and EDC (669 mg, 1.3 eq) was added and the flask was cooled to 0° C. DIEA (1.04 g, 3 equiv.) was slowly added and the reaction was stirred at room temperature overnight. The solvent was removed under vacuum and the residue was purified by column chromatography with 5% methanol in dichloromethane to give 15U as a solid (865 mg, 79%).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified by column chromatography with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-e62b1632ec91467cbfcaff3b8013fed3
Source dataset
uspto-grants-2012_04
Patent number
US08148367B2

Reaction notes

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