Hydrochloric Acid → HCID 69655753, compound

HRID 2214700Notes

Reaction equation

HRID 2214700 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:5][NH:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.[CH3:21][C:22]1([CH3:32])[O:26][C:25](=[CH:27][C:28](Cl)=[O:29])[C:24](=[O:31])[O:23]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:5][N:6]([CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:28](=[O:29])[CH:27]=[C:25]1[C:24](=[O:31])[O:23][C:22]([CH3:21])([CH3:32])[O:26]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 21947437HCID 21947437, compoundHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 69655753HCID 69655753, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of (3,4-dichloro-benzyl)-(3-phenyl-propyl)-amine; hydrochloride (330 mg, 1.0 mmol) and (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride (206 mg, 1.08 mmol) in CH2Cl2 (10 mL) at room temperature was added diisopropylethylamine (386 μL, 2.2 mmol). After 30 min, the reaction mixture was diluted with ether (50 mL), washed with dilute aqueous HCl (1×5 mL), water (1×10 mL), and saturated aq. NaCl (1×5 mL). The organic layer was dried over Na2SO4, filtered and concentrated to give the desired amide (447 mg, 100% yield) as a viscous oil. 1H NMR (300 MHz, CDCl3) δ: 7.41–6.94 (8H, m), 6.08 (0.66H, s), 6.01 (0.34H, s), 4.53 (1.33H, s), 4.48 (0.67H, s), 3.41 (0.67H, t, J=7.5 Hz), 3.26 (1.33H, t, J=7.8 Hz), 2.61 (2H, t, J=7.3 Hz), 1.95–1.85 (2H, m), 1.71 (6H,s). MS calcd for C23H23Cl2NO4Na (M+Na): 470.09. Found: 470.09.

Workup

  1. washwashed with dilute aqueous HCl (1×5 mL), water (1×10 mL), and saturated aq. NaCl (1×5 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a170eee04de347a1be18cb7b6f948e63
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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