1,2-Dichloroethane → HCID 69593474, compound

HRID 1825052Notes

Reaction equation

HRID 1825052 reaction equation
Cl.[NH2:2][C@H:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:7]=1)[CH2:4][OH:5].[C:18](O)(=[O:27])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(Cl)CCl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[OH:5][CH2:4][C@H:3]([NH:2][C:18](=[O:27])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:7]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 87842-Propenoic acid, 3-phenyl-HCID 69527946HCID 69527946, compound

Product 1

HCID 69593474HCID 69593474, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Mixture of (R)-2-Amino-2-(3-morpholin-4-yl-phenyl)-ethanol hydrochloride (70 mg, 0.24 mmol), cinnamic acid (35 mg, 0.24 mmol), EDC (91 mg, 0.47 mmol), DMAP (29 mg, 0.24 mmol), triethyl amine (0.13 mL, 0.95 mmol) in dichloromethane (1 mL) was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and purified by flash chromatography with 60% acetone/hexanes to provide the title compound as a white solid (57 mg, 68% yield).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompurified by flash chromatography with 60% acetone/hexanes

Sources & evidence

ORD record
ord-fca2dfd899ee4d4baaaa57f7161cc4f1
Source dataset
uspto-grants-2006_05
Patent number
US07045551B2

Reaction notes

Loading…