Methanesulfonic Acid → 5-[(4-Aminobutoxy)methyl]-N,N-dimethyl-2-furanmethanamine

HRID 35044

Reaction equation

HRID 35044 reaction equation
CS(O)(=O)=O.[CH3:6][N:7]([CH2:9][C:10]1[O:14][C:13]([CH2:15][OH:16])=[CH:12][CH:11]=1)[CH3:8].[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21]O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O>[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:16][CH2:15][C:13]1[O:14][C:10]([CH2:9][N:7]([CH3:6])[CH3:8])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 258684-Amino-1-butanolHCID 849065-((Dimethylamino)methyl)-2-furanmethanol

Product 1

HCID 212975835-[(4-Aminobutoxy)methyl]-N,N-dimethyl-2-furanmethanamineYield 29.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methanesulphonic acid (86 g), 5-[(dimethylamino)methyl]-2-furanmethanol (15.5 g) and 4-aminobutanol (17.8 g) in dry tetrahydrofuran was heated at 100° for 11/2 h. Excess sodium carbonate was added to the cooled solution, the suspension was filtered and the filtrate was evaporated to give a red oil which was dissolved in water and extracted with ether. The extract was distilled to give the title compound as an oil (6.6 g) b.p. 100°-110°, 0.08 mm. TLC silica, methanol/ammonia 0.88 80:1, Rf 0.3.

Workup

  1. temperaturewas heated at 100° for 11/2 h
  2. filtrationthe suspension was filtered
  3. customthe filtrate was evaporated
  4. customto give a red oil which
  5. extractionextracted with ether
  6. distillationThe extract was distilled

Sources & evidence

ORD record
ord-c405c788e86d4234a8a437fe7eab9832
Source dataset
uspto-grants-1988_08
Patent number
US04764612

Linked notes

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