Triethylamine → HCID 67281317, compound

HRID 2408425Notes

Reaction equation

HRID 2408425 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:24][C:25](=[O:27])[NH2:26])[CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:36]([O:38][CH2:39][CH3:40])=[O:37]>CC(C)=O.O>[CH2:39]([O:38][C:36](=[O:37])[O:23][C:20]1[CH:21]=[CH:22][C:17]([N:14]2[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][CH:8]([O:24][C:25](=[O:27])[NH2:26])[C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:12][CH2:13]2)=[CH:18][CH:19]=1)[CH3:40]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 67280973HCID 67280973, compound

Product 1

HCID 67281317HCID 67281317, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

The compound ‘carbamic acid 1-(4-fluoro-phenyl)-3-[4-(4-hydroxy-phenyl)-piperazin-1-yl]-propyl ester (0.93 mmol) prepared in Example 88 was dissolved in acetone (15 mL), and triethylamine (1.86 mmol) was added and ethyl chloroformate (2.4 mmol) was added dropwise, and the resulting mixture was then stirred at a room temperature for 5 hours. The reaction mixture was diluted with water, and extracted several times with ethyl acetate to obtain an organic phase. The prepared organic phase was dried over magnesium sulfate, and concentrated under a reduced pressure. The resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1) to obtain a title compound.

Workup

  1. extractionextracted several times with ethyl acetate
  2. customto obtain an organic phase
  3. dry with materialThe prepared organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customThe resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-0f334d68be0542ccbbc9225656451981
Source dataset
uspto-grants-2014_08
Patent number
US08815852B2

Reaction notes

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