1,2-Dichloroethane → (S)-N-{1-[3-(2-Methyl-morpholin-4-yl)-phenyl]ethyl}-3-phenyl-acrylamide

HRID 2307454Notes

Reaction equation

HRID 2307454 reaction equation
Cl.[CH3:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]2[CH:10]=[C:11]([C@@H:15]([NH2:17])[CH3:16])[CH:12]=[CH:13][CH:14]=2)[CH2:4]1.[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>[CH3:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]2[CH:10]=[C:11]([C@@H:15]([NH:17][C:18](=[O:27])[CH:19]=[CH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:16])[CH:12]=[CH:13][CH:14]=2)[CH2:4]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 87842-Propenoic acid, 3-phenyl-HCID 69851400(S)-1-[3-(2-methyl-morpholin-4-yl)-phenyl]-ethylamine Hydrochloric acid Salt

Product 1

HCID 69919582(S)-N-{1-[3-(2-Methyl-morpholin-4-yl)-phenyl]ethyl}-3-phenyl-acrylamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Mixture of (S)-1-[3-(2-methyl-morpholin-4-yl)-phenyl]-ethylamine hydrochloric acid salt, Preparation 41(30 mg, 0.10 mmol), cinnamic acid (17 mg, 0.11 mmol), EDC (40 mg, 0.20 mmol), DMAP (13 mg, 0.10 mmol), triethylamine (0.06 ml, 0.40 mmol) in dichloromethane (0.5 mL) was stirred at room temperature overnight. The reaction mixture was purified by filtering through 2 g silica-gel syringe with 70% ethyl acetate/hexanes. The filtrate was concentrated under vacuum to provide the title compound as a yellow solid.

Workup

  1. customThe reaction mixture was purified
  2. filtrationby filtering through 2 g silica-gel syringe with 70% ethyl acetate/hexanes
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-82f1bdb3e16b45d39658f711d23316fa
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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