N-Methylethylamine → (S)-3-(1-{4-[4-(4-Ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethyl)-1-ethyl-1-methyl-urea

HRID 1617326Notes

Reaction equation

HRID 1617326 reaction equation
Cl.[CH2:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C@@H:23]([NH2:25])[CH3:24])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH3:3].C1C[CH2:35][N:34]2[C:29](=NCC[CH2:33]2)[CH2:28]C1.C(NC)C.[O:41]1CCOCC1>>[CH2:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[CH2:12][CH2:13][N:14]([C:17]3[CH:18]=[CH:19][C:20]([C@@H:23]([NH:25][C:33](=[O:41])[N:34]([CH2:29][CH3:28])[CH3:35])[CH3:24])=[CH:21][CH:22]=3)[CH2:15][CH2:16]2)=[CH:9][CH:10]=1)[CH3:3]

Participants

5

Reactant 4

HCID 12219N-MethylethylamineHCID 312751,4-Dioxane2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86688559(S)-1-{4-[4-(4-ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethylamine hydrochloride

Product 1

HCID 71617630(S)-3-(1-{4-[4-(4-Ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethyl)-1-ethyl-1-methyl-urea

Procedure

To 36 mg (0.10 mmol) (S)-1-{4-[4-(4-ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethylamine hydrochloride (XII.1) in 1.5 mL 1,4-dioxane are added 37 μL (0.25 mmol) DBU and 33 mg (0.20 mmol) CDT. The mixture is stirred for 5 min at rt. Subsequently 7.1 mg (0.12 mmol) ethyl-methyl-amine in 1.0 mL 1,4-dioxane are added and stirring is continued for 12 h at rt. The solvent is removed under reduced pressure, the residue is taken up in DMF and purified by HPLC (Sunfire, narrow gradients, water (+0.1% TFA)/methanol) to yield the desired product.

Workup

  1. stirringstirring
  2. waitis continued for 12 h at rt
  3. customThe solvent is removed under reduced pressure
  4. custompurified by HPLC (Sunfire, narrow gradients, water (+0.1% TFA)/methanol)

Sources & evidence

ORD record
ord-4a76c84d0a1c4703b9f5336f7cedaf92
Source dataset
uspto-grants-2014_07
Patent number
US08765959B2

Reaction notes

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