Formic Acid → HCID 22809548, compound

HRID 1448071Notes

Reaction equation

HRID 1448071 reaction equation
[CH2:1]([N:8](C)[C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18]([OH:20])=O.[OH-].[Na+].[CH3:23]C1C=CC(S(O)(=O)=O)=CC=1>CCOCC>[CH2:1]([N:8]([C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[N:15]([CH3:16])[CH3:23])[CH:18]=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 54247994HCID 54247994, compound

Product 1

HCID 22809548HCID 22809548, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of trans-N-benzyl-N,N'-dimethyl-1,2-cyclohexanediamine (9.29 g.; 0.04 mole) in 40 ml. of formic acid was refluxed 20 hours, added and poured into 200 g. of ice. It was basified with 15% NaOH and extracted well with ether. The extract was washed with H2O, saturated salt solution, dried (MgSO4) and evaporated. The residue (9.7 g.) was converted to the salt with 2 mole of p-TSA in ether. The resulting gum was crystallized from MeOH-ether to give 13.64 g.; of the titled compound, m.p. 201°-202.5°. The analytical sample melted at 202°-203°. uv sh 210 nm (ε 27,850); sh 222 (25,600); sh 227 (12,350); sh 243 (302); sh 248 (375); λ max 254 (472); 258 (556); 261 (562); 268 (399); sh 272 (175). ir N + H 2720, 2560; C=O 1670, 1650; C=C 1600, 1495; SO3 /ether 1225, 1170, 1120, 1030, 1010, 815, 705, 685. nmr in D2O (100 MHz) was in accord. Mass spectrum M+ 260.

Workup

  1. additionadded
  2. additionpoured into 200 g
  3. extractionextracted well with ether
  4. washThe extract was washed with H2O, saturated salt solution
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe resulting gum was crystallized from MeOH-ether
  8. customto give 13.64 g

Sources & evidence

ORD record
ord-149325d0ea3844d2b41092afd9d562e9
Source dataset
uspto-grants-1979_12
Patent number
US04179501

Reaction notes

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