Toluene → HCID 86663380, compound

HRID 1193358Notes

Reaction equation

HRID 1193358 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[NH:10][C@H:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([N:17]2[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(C)C)(=O)C.C1(C)C=CC=CC=1.[C@:39]12([CH2:49][S:50]([OH:53])(=[O:52])=[O:51])[C:46]([CH3:48])([CH3:47])[CH:43]([CH2:44][CH2:45]1)[CH2:42][C:40]2=[O:41]>O>[CH3:47][C:46]1([CH3:48])[C@@H:43]2[CH2:44][CH2:45][C@@:39]1([CH2:49][S:50]([OH:53])(=[O:52])=[O:51])[C:40](=[O:41])[CH2:42]2.[CH3:23][N:20]1[CH2:19][CH2:18][N:17]([C@@H:13]2[CH2:14][CH2:15][CH2:16][C@H:11]([NH:10][C:9](=[O:24])[O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:12]2)[CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 7915Isopropyl AcetateHCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 58235963HCID 58235963, compound

Product 1

HCID 86663380HCID 86663380, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of (cis)-benzyl-3-(4-methylpiperazin-1-yl)cyclohexylcarbamate (2.0 g, 6.04 mmol, 1.0 eq.), isopropyl acetate (12 ml) and toluene (2.5 ml) was heated for 15 minutes at 65° C. (1S)-(+) Camphorsulfonic acid (700 mg, 3.02 mmol, 0.5 eq.) and water (0.1 ml) were added at RT and the mixture was heated for 3 hours at 75° C. Stirring was then carried out for 3 hours at RT and the mixture was subsequently allowed to stand overnight at RT for crystallization. The resulting precipitate was filtered off and washed with isopropyl acetate (20 ml). For purification, the desired product was recrystallized from ethanol/isopropyl acetate. Yield: 14% (500 mg, 0.888 mmol)

Workup

  1. additionwere added at RT
  2. customto stand overnight at RT for crystallization
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with isopropyl acetate (20 ml)
  5. customFor purification
  6. customthe desired product was recrystallized from ethanol/isopropyl acetate

Sources & evidence

ORD record
ord-f3fcd0da2aae4c969921caae5885a908
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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