Benzylethanolamine → Benzenemethanamine, N-(2-chloroethyl)-, hydrochloride (1:1)

HRID 581807Notes

Reaction equation

HRID 581807 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:14])=O>C(Cl)(Cl)Cl>[ClH:14].[CH2:1]([NH:8][CH2:9][CH2:10][Cl:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4348BenzylethanolamineHCID 24386Thionyl Chloride

Product 1

HCID 13054189Benzenemethanamine, N-(2-chloroethyl)-, hydrochloride (1:1)

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of N-benzyl-2-aminoethanol (12, 79.05 g, 0.523 mole) in chloroform (400 niL) was treated with thionyl chloride (80 mL, 1.09 mole) at room temperature. The resulting mixture was heated to reflux (6 h). The solvent was removed in vacuo, the residue dissloved in hot ethanol (1.3 L) and cooled overnight. The solids were collected via suction filtration and dried in vacuo at 65° C. (24 h) to afford the title compound 13 as white plates.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux (6 h)
  3. customThe solvent was removed in vacuo
  4. temperaturecooled overnight
  5. filtrationThe solids were collected via suction filtration
  6. customdried in vacuo at 65° C. (24 h)

Sources & evidence

ORD record
ord-f06f7d0bd63041069f897055c7083c2e
Source dataset
uspto-grants-1999_07
Patent number
US05922722

Reaction notes

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