Hydrochloric Acid → HCID 66845470, compound

HRID 254258Notes

Reaction equation

HRID 254258 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)CCN)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:19]([CH2:22]C)CC)C.Cl[CH2:25][C:26](Cl)=[O:27].[ClH:29]>C(Cl)Cl>[Cl:29][CH2:22][NH:19][C:26](=[O:27])[CH2:25][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 796983,3-Diphenylpropylamine

Product 1

HCID 66845470HCID 66845470, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1 g (4.73 mmol, 1 eq.) of 3,3-diphenylpropylamine and 732 μL (5.21 mmol, 1.1 eq.) of triethylamine are diluted in 30 mL of DCM at 0° C. under argon. 300 μL (3.77 mmol, 0.8 eq.) of chloroacetyl chloride are added dropwise. White fumes form then gradually dissipate. The mixture is stirred for 45 min. at 0° C., the solution becomes red. A dilute HCl solution is added then the aqueous phase is extracted with DCM. The organic phase is washed once with water then once with brine, dried over MgSO4, filtered and concentrated. The product is obtained in the form of oil (m=1.36 g, yield=100%).

Workup

  1. customWhite fumes form
  2. extractionthe aqueous phase is extracted with DCM
  3. washThe organic phase is washed once with water
  4. dry with materialonce with brine, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product is obtained in the form of oil (m=1.36 g, yield=100%)

Sources & evidence

ORD record
ord-a3475723c64845fb8bb074cbb37350c6
Source dataset
uspto-grants-2011_01
Patent number
US07875609B2

Reaction notes

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