Methanol → 2-(Benzylamino)ethyl hydrogen sulfate

HRID 1375049Notes

Reaction equation

HRID 1375049 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COCCOCCOC.[S:21](=O)(=[O:24])([OH:23])[OH:22].CO>O.C1(C)C=CC=CC=1>[S:21]([OH:24])([O:11][CH2:10][CH2:9][NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:23])=[O:22]

Participants

7

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 4348BenzylethanolamineHCID 8150Diglyme

Product 1

HCID 218250682-(Benzylamino)ethyl hydrogen sulfate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of N-benzylethanolamine (302 g) in a mixture of water (8.92 ml) and toluene (1510 ml) and diglyme (151 ml) was added dropwise sulfuric acid (128 ml) over 30 minutes, and the mixture was stirred under reflux for 6 hours. After cooled to room temperature, to the mixture was added methanol (300 ml), and then the mixture was stirred for 1 hour. The precipitate was filtered and washed with methanol (300 ml×4), and dried to give 2-(N-benzylamino)ethyl hydrogen sulfate (352.6 g) as a white powder.

Workup

  1. temperatureunder reflux for 6 hours
  2. stirringthe mixture was stirred for 1 hour
  3. filtrationThe precipitate was filtered
  4. washwashed with methanol (300 ml×4)
  5. customdried

Sources & evidence

ORD record
ord-742ddaa7f2ad4a88a23776431c1cc4eb
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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