1,1'-(Azodicarbonyl)dipiperidine → 4-{1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile

HRID 1743723Notes

Reaction equation

HRID 1743723 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.O[CH:16]([C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1)[CH2:17][CH:18]=[CH2:19].C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1(C)C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:16]([C:20]2[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=2)[CH2:17][CH:18]=[CH2:19])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 110193454-(1-Hydroxy-3-butenyl)benzonitrileHCID 117455194-[(Oxan-2-yl)oxy]phenol

Product 1

HCID 222356714-{1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrileYield 68.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

4-(Tetrahydro-2H-pyran-2-yloxy)phenol (19.0 g, 0.1 mol) and 4-(1-hydroxy-3-butenyl)benzonitrile (17.8 g, 0.1 mol) was mixed in toluene, and cooled to 0° C. (under nitrogen). TBP (22.9 g, 0.11 mol) was added, followed by ADDP. The mixture was stirred at rt overnight, filtered, and evaporated. Purification by chromatography on silica gave 24 g (68.7%) of the desired compound.

Workup

  1. additionTBP (22.9 g, 0.11 mol) was added
  2. filtrationfiltered
  3. customevaporated
  4. customPurification by chromatography on silica

Sources & evidence

ORD record
ord-c55d5a9310124f4fb97feca2aff36e68
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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