Toluene → HCID 11682096, compound

HRID 656323Notes

Reaction equation

HRID 656323 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Al](C)C.C1(C)C=CC=CC=1.[CH3:19][C:20]1([C:35](OCC)=[O:36])[CH2:25][CH2:24][CH2:23][N:22]([S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:21]1>C(Cl)Cl>[CH:1]1([NH:7][C:35]([C:20]2([CH3:19])[CH2:25][CH2:24][CH2:23][N:22]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:27])=[O:28])[CH2:21]2)=[O:36])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 7965CyclohexylamineHCID 16682925TrimethylaluminumHCID 66743543HCID 66743543, compound

Product 1

HCID 11682096HCID 11682096, compoundYield 3.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At r.t., to a solution of cyclohexanamine (19.1 mg, 0.19 mmol) in methylene chloride (0.1 mL) was added 2.0 M of trimethylaluminum in toluene (96 ul, 0.19 mmol). After stirring for 30 min, to the solution was added a solution of ethyl 3-methyl-1-(phenylsulfonyl)piperidine-3-carboxylate (35 mg, 0.11 mmol) in methylene chloride (0.1 mL). The mixture was stirred at r.t for 10 min, then, at 40° C. overnight. After cooling to r.t., the mixture was purified with combi-flash. The product was further purified with prep. HPLC. 1.3 mg final product was obtained. Yield: 3.2%. LCMS: m/z 365.1 (M+H)+; 751.3 (2M+Na)+.

Workup

  1. stirringThe mixture was stirred at r.t for 10 min
  2. customat 40° C.
  3. customovernight
  4. customthe mixture was purified with combi-flash
  5. customThe product was further purified with prep

Sources & evidence

ORD record
ord-c3a4a9a683c348c1bd356924d726fb50
Source dataset
uspto-grants-2011_12
Patent number
US08071624B2

Reaction notes

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