Chloroacetyl chloride → HCID 86623719, compound

HRID 249854Notes

Reaction equation

HRID 249854 reaction equation
Cl[CH2:2][C:3]([Cl:5])=[O:4].[CH2:6]([NH:13][C@H:14]([CH3:17])[CH2:15][OH:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:6]([NH:13][C@H:14]([CH3:17])[CH2:15][O:16][CH2:2][C:3]([Cl:5])=[O:4])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 7353896(2R)-2-(Benzylamino)propan-1-ol

Product 1

HCID 86623719HCID 86623719, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Chloroacetyl chloride (11.6 mL, 120 mmol) was added dropwise at 0° C. to a solution of (R)-2-(benzylamino)propan-1-ol (19.9 g, 120 mmol) and triethylamine (30.5 mL) in toluene (600 mL). The cooling bath was removed and the reaction mixture was stirred at room temperature for 18 h. The reaction was concentrated under reduced pressure and the recovered solids dissolved in EtOAc (500 mL) and then washed with saturated bicarbonate (2×250 mL), H2O (250 mL) and saturated brine (250 mL). The organic phase was then dried (Na2SO4), filtered and concentrated to afford (R)-2-(2-(benzylamino)propoxy)acetyl chloride: MS consistent.

Workup

  1. customThe cooling bath was removed
  2. concentrationThe reaction was concentrated under reduced pressure
  3. dissolutionthe recovered solids dissolved in EtOAc (500 mL)
  4. washwashed with saturated bicarbonate (2×250 mL), H2O (250 mL) and saturated brine (250 mL)
  5. dry with materialThe organic phase was then dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3cd8fafccf3a42d8990799337093fa76
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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