p-Toluenesulfonic acid → HCID 86736411, compound

HRID 614570Notes

Reaction equation

HRID 614570 reaction equation
[CH2:1]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[N:15]([CH3:17])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18](N)C1C=CC=CC=1.[OH-:26].[Na+].[CH3:28][C:29]1[CH:30]=[CH:31][C:32]([S:35]([OH:38])(=[O:37])=[O:36])=[CH:33][CH:34]=1>CCOCC.C(O)=O>[C:29]1([CH3:28])[CH:30]=[CH:31][C:32]([S:35]([OH:38])(=[O:36])=[O:37])=[CH:33][CH:34]=1.[CH2:1]([N:8]([C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[N:15]([CH3:17])[CH3:16])[CH:18]=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 54124468HCID 54124468, compound

Product 1

HCID 86736411HCID 86736411, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of trans-N-benzyl-N',N'-dimethyl-1,2-cyclohexanediamine (9.29 g., 0.04 mole) prepared as in Procedure IV, but using benzylamine instead of benzylmethylamine, in 40 ml. of formic acid is refluxed 20 hr., and poured into 200 g. of ice. It is basified with 15% NaOH and extracted well with ether. The extract is washed with H2O and with saturated salt solution, is dried (MgSO4) and evaporated. The residue is converted with 2 mole of p-TSA in ether. The resulting gum is crystallized from MeOH-ether to give 13.64 g. of title compound, m.p. 201°-201.5°. The analytical sample melts at 202°-203°. uv:sh 210 nm (ε 27,850); sh 222 (25,600); sh 227 (12,350); sh 243 (302); sh 248 (375); λmax 254 (472); 258 (556); 261 (562); 268 (399); sh 272 (175). ir:NH 2720, 2560; C=O 1670, 1650; C=C 1600, 1495; SO3 /other 1225, 1170, 1120, 1030, 1010, 815, 705, 685. nmr in D2O (100 MHz) is in accord. Mass spectrum M+ 260.

Workup

  1. addition, and poured into 200 g
  2. extractionextracted well with ether
  3. washThe extract is washed with H2O and with saturated salt solution
  4. dry with materialis dried (MgSO4)
  5. customevaporated
  6. customThe resulting gum is crystallized from MeOH-ether
  7. customto give 13.64 g

Sources & evidence

ORD record
ord-c3a5955e8cc44714b7b6e1da9f1f83aa
Source dataset
uspto-grants-1979_03
Patent number
US04145435

Reaction notes

Loading…