Methanesulfonic Acid → HCID 22884198, compound

HRID 1598018Notes

Reaction equation

HRID 1598018 reaction equation
[C@H:1]1([NH2:8])[CH2:6][CH2:5][CH2:4][C@@H:3]([NH2:7])[CH2:2]1.Cl[C:10]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[N:13]=[CH:12][CH:11]=1.CS(O)(=O)=O>CN1CCCC1=O.C(#N)C>[Cl:20][C:16]1[CH:15]=[C:14]2[C:19]([C:10]([NH:7][C@H:3]3[CH2:4][CH2:5][CH2:6][C@@H:1]([NH:8][C:10]4[C:19]5[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=5)[N:13]=[CH:12][CH:11]=4)[CH2:2]3)=[CH:11][CH:12]=[N:13]2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 68664,7-DichloroquinolineHCID 6998900(1R,3S)-1β,3β-Cyclohexanediamine

Product 1

HCID 22884198HCID 22884198, compoundYield 21.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

23.2 g of cis-cyclohexane-1,3-diamine and 80.5 g of 4,7-dichloroquinoline are reacted at 150° C. in 400 ml of N-methyl-2-pyrrolidone under argon for 24 hours. After cooling insoluble material is filtered off and the filtrate is treated with 600 ml of water. The separated crude product is introduced into 400 ml of water and 100 ml of glacial acetic acid. The mixture is extracted three times with 200 ml of ethyl acetate each time and then adjusted to pH 12 by the addition of 600 ml of 2N NaOH. The separated crystalline diamine is recrystallized from 270 ml of dimethylformamide, 20.1 g of pure product being obtained. This is converted into the dimethanesulphonate in 200 ml of boiling acetonitrile with 6.4 ml of methanesulphonic acid. 19.5 g of colourless crystalline salt, m.p.:>250° C., are obtained.

Workup

  1. temperatureAfter cooling insoluble material
  2. filtrationis filtered off
  3. additionthe filtrate is treated with 600 ml of water
  4. customThe separated crude product
  5. additionis introduced into 400 ml of water and 100 ml of glacial acetic acid
  6. extractionThe mixture is extracted three times with 200 ml of ethyl acetate each time
  7. additionadjusted to pH 12 by the addition of 600 ml of 2N NaOH
  8. customThe separated crystalline diamine is recrystallized from 270 ml of dimethylformamide, 20.1 g of pure product
  9. custombeing obtained

Sources & evidence

ORD record
ord-4a4b058b17bf4b67a5c4bb8a322e358b
Source dataset
uspto-grants-1998_04
Patent number
US05736557

Reaction notes

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