Triethylamine → Cycloheptylurea

HRID 582570Notes

Reaction equation

HRID 582570 reaction equation
C(C1C=C([N:9]([CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:10]([NH:12]C2CCNCC2)=[O:11])C=CC=1)#N.C(N(CC)CC)C.C1(CS(Cl)(=O)=O)C=CC=CC=1>O1CCCC1>[CH:19]1([NH:9][C:10]([NH2:12])=[O:11])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 54268872N-(3-Cyanophenyl)-N'-(piperidin-4-yl)cycloheptylurea

Product 1

HCID 294522CycloheptylureaYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-(3-Cyanophenyl)-N'-(piperidin-4-yl)cycloheptylurea (2.07 g, 6.95 mmol) in tetrahydrofuran (100 ml) with triethylamine (7.64 mmol, 0.77 g, 1.1 ml) was cooled to 0° C. and a-toluenesulfonyl chloride (1.46 g, 7.64 mmol) in tetrahydrofuran (60 ml) was added dropwise. The reaction was allowed to cool to ambient temperature and was stirred for 18 h. The solvent was removed in vacuo and the residue patitioned between water and 5:1 ethyl acetate:acetone. The organic layer was washed with 1N HCl and 1N NaOH, then brine. It was dried (Na2SO4) and evaporated to give 2.63 g of crude product. Purification by medium pressure liquid chromatography on a silica gel column (350 g) gave N-(3-cyanophenyl)-N'-(1-((phenyl)methane)sulfonyl)piperidin-4-yl)cycloheptylurea (1.81 g, 4.0 mmol, 58%, mp 203-204° C.); HRMS (M+H)+ calc. 453.196038, found 453.198085.

Workup

  1. customThe solvent was removed in vacuo
  2. washThe organic layer was washed with 1N HCl and 1N NaOH
  3. dry with materialIt was dried (Na2SO4)
  4. customevaporated
  5. customto give 2.63 g of crude product
  6. customPurification by medium pressure liquid chromatography on a silica gel column (350 g)

Sources & evidence

ORD record
ord-3ce6f61502364df3bc47bfb0ac82ee75
Source dataset
uspto-grants-1999_07
Patent number
US05925635

Reaction notes

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