Ammonia → HCID 19095359, compound

HRID 486592Notes

Reaction equation

HRID 486592 reaction equation
[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]3[C:18]4[N:17]5[CH2:19][CH2:20][N:21]=[C:22]([CH3:23])[C:16]5=[CH:15][C:14]=4[CH2:13][CH2:12][C:11]=3[CH:24]=2)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.CS(O)(=O)=O.N.[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35]>CO.C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35].[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]3[C:18]4[N:17]5[CH2:19][CH2:20][N:21]=[C:22]([CH3:23])[C:16]5=[CH:15][C:14]=4[CH2:13][CH2:12][C:11]=3[CH:24]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 6395Methanesulfonic AcidHCID 444972Fumaric AcidHCID 19095292HCID 19095292, compound

Product 1

HCID 19095359HCID 19095359, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

3-Cyclohex-2-enyl-5,6,10,11-tetrahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole (1.05 g) was dissolved in 100 ml of methanol and treated with 0.2 ml of methanesulphonic acid. After the addition of 100 mg of tris(triphenylphosphine)-rhodium-(I) chloride the mixture was hydrogenated at room temperature for 24 hours. The mixture was freed from solvent, treated with 100 ml of 10% ammonia solution and extracted three times with 100 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 0.95 g of yellow oil, was dissolved in a 20-fold amount of ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. After concentration to a volume of about 16 ml and addition of 30 ml of ethyl acetate there separated 0.57 g of yellow crystals which were recrystallized from an ethanol/ethyl acetate mixture (1:2). There was obtained 0.39 g (37%) of 3-cyclohexyl-5,6,10,11 -tetrahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole fumarate (1:1); m.pt.: 165°-167° C. (dec.).

Workup

  1. extractionextracted three times with 100 ml of methylene chloride each time
  2. dry with materialdried with MgSO4
  3. dissolutionThe residue, 0.95 g of yellow oil, was dissolved in a 20-fold amount of ethanol
  4. concentrationAfter concentration
  5. additionto a volume of about 16 ml and addition of 30 ml of ethyl acetate there separated 0.57 g of yellow crystals which
  6. customwere recrystallized from an ethanol/ethyl acetate mixture (1:2)

Sources & evidence

ORD record
ord-ff4ff84e155f48e8b544c6ec36a2a163
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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