Hydrochloric Acid → (4-(2-Chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate hydrochloride

HRID 655949Notes

Reaction equation

HRID 655949 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][NH:5][C:6]([C:8]1([CH2:21][OH:22])[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1)=[O:7].[CH2:27]([C:29]1[CH:34]=[CH:33][C:32]([N:35]=[C:36]=[O:37])=[CH:31][CH:30]=1)[CH3:28].Cl.O1CCOCC1>C1COCC1.CN(C1C=CN=CC=1)C.CO>[ClH:1].[CH2:27]([C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:37])[O:22][CH2:21][C:8]2([C:6](=[O:7])[NH:5][CH2:4][C:3]3[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=3[Cl:1])[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[CH:31][CH:30]=1)[CH3:28]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 900074-Ethylphenyl isocyanateHCID 59778532Tert-butyl 4-(2-chlorobenzylcarbamoyl)-4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 69162882(4-(2-Chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate hydrochlorideYield 151.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-(2-chlorobenzylcarbamoyl)-4-(hydroxymethyl)piperidine-1-carboxylate (1.8 g, 4.8 mmol) in THF were added DMAP (118 mg, 0.9 mmol, 0.1 equiv.) and 4-ethylphenylisocyanate (1.1 mL, 7.3 mmol, 1.5 equiv.) at r. t. The reaction mixture was stirred for 1 h. The reaction mixture was concentrated to dryness. To a solution of the above product in CH3OH was added 4M HCl in dioxane (3.6 mL, 3 equiv.), which was stirred overnight. The white solid was filtered and dried to give (4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate hydrochloride (1.7 g, 81%). LRMS (M-Boc+H+) m/z 430.1.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. stirringwas stirred overnight
  3. filtrationThe white solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-ef3e93dd584441b6980db12e10372fda
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Reaction notes

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