1,4-Dioxane → HCID 67971077, compound

HRID 1470757Notes

Reaction equation

HRID 1470757 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:21]=[CH:20][C:19]([C@@H:22]([NH2:24])[CH3:23])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)[CH3:2].[CH2:25]1[CH2:35][CH2:34][N:33]2[C:28](=NCC[CH2:32]2)CC1.C1(NC)CC1.[O:41]1CCOCC1>>[CH:34]1([N:33]([CH3:28])[C:32]([NH:24][C@H:22]([C:19]2[CH:18]=[CH:17][C:16]([CH:13]3[CH2:12][CH2:11][N:10]([C:7]4[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:9][CH:8]=4)[CH2:15][CH2:14]3)=[CH:21][CH:20]=2)[CH3:23])=[O:41])[CH2:25][CH2:35]1

Participants

5

Reactant 4

HCID 312751,4-DioxaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11029756N-MethylcyclopropanamineHCID 67125458HCID 67125458, compound

Product 1

HCID 67971077HCID 67971077, compound

Procedure

To 32.5 mg (0.10 mmol) (S)-1-{4-[1-(4-ethoxy-phenyl)-piperidin-4-yl]-phenyl}-ethylamine (XIII.1) in 1.5 mL dioxane, 30 μL (0.20 mmol) DBU and 33 mg (0.20 mmol) CDT are added at rt and the mixture is stirred for 5 min. Subsequently 8.5 mg (0.15 mmol cyclopropyl-methyl-amine are added and stirring is continued over night. The mixture is concentrated in vacuo. The residue is purified using reversed phase column chromatography (water+0.1% TFA:MeOH) and the corresponding fractions are concentrated to yield the desired product.

Workup

  1. stirringstirring
  2. waitis continued over night
  3. concentrationThe mixture is concentrated in vacuo
  4. customThe residue is purified
  5. concentrationthe corresponding fractions are concentrated

Sources & evidence

ORD record
ord-cb1989622e424b4db2eda14ab52c0bdb
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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