Chloroacetyl chloride → HCID 45139974, compound

HRID 574295Notes

Reaction equation

HRID 574295 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([NH:13][CH2:14][CH2:15][CH3:16])[CH2:10]2)=[CH:5][CH:4]=1.CCN(CC)CC.[Cl:24][CH2:25][C:26](Cl)=[O:27].[OH-].[Na+]>C(Cl)Cl>[Cl:24][CH2:25][C:26]([N:13]([CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:10]1)[CH2:14][CH2:15][CH3:16])=[O:27]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 100821727-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine

Product 1

HCID 45139974HCID 45139974, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 32a (HCl salt, 5.0 g, 19.5 mmol) and Et3N (5.5 ml, 39.1 mmol) was stirred at 0° C. in CH2Cl2 (65 ml) for 15 min. Chloroacetyl chloride (1.9 ml, 23.5 mmol) was added dropwise and the resulting solution was stirred at room temperature for 20 min, at which time the reaction mixture was poured into a 1M solution of NaOH (50 ml) and the product was extracted with dichloromethane, dried (Na2SO4), filtered, and concentrated. The crude material was purified by column chromatography (Hex:EtOAc, 3:1) to give 5.5 g (95%) of 33a. 1H NMR (400 MHz, CDCl3) 0.90-0.98 (m, 3H), 1.64-1.72 (m, 2H), 3.19-3.27 (m, 2H), 4.00 (s, 3H), 6.61-6.62 (dd, 1H, J=1.6 Hz), 6.64-6.77 (m, 1H), 6.96-6.99 (d, 1H, J=8.8 Hz).

Workup

  1. extractionthe product was extracted with dichloromethane
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by column chromatography (Hex:EtOAc, 3:1)

Sources & evidence

ORD record
ord-29ded24c8343452cbd8666c5ba07f759
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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