N-[4-(hydroxymethyl)phenyl]acrylamide → HCID 178483936, compound

HRID 630406Notes

Reaction equation

HRID 630406 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:13])[CH:11]=[CH2:12])=[CH:5][CH:4]=1.[OH:14][C:15]([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)([C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)[C:16]([O:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([NH:25][CH3:26])[CH2:21][CH2:20]1)=[O:17]>O1CCCC1>[OH:14][C:15]([C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)[C:16]([O:18][C@H:19]1[CH2:20][CH2:21][C@H:22]([N:25]([CH2:12][CH2:11][C:10]([NH:9][C:6]2[CH:5]=[CH:4][C:3]([CH2:2][OH:1])=[CH:8][CH:7]=2)=[O:13])[CH3:26])[CH2:23][CH2:24]1)=[O:17]

Participants

4

Reactant 2

HCID 13661541N-[4-(hydroxymethyl)phenyl]acrylamide2×HCID 178484861HCID 178484861, compound2×

Product 1

HCID 178483936HCID 178483936, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of N-[4-(hydroxymethyl)phenyl]acrylamide (intermediate 79; 0.3 g, 1.7 mmol) in tetrahydrofuran (6 mL) was added trans-4-(methylamino)cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 5; 0.5 g, 1.42 mmol). The mixture was placed in a sealed vessel and stirred for 4 days at 75° C. The solvent was removed under reduced pressure and the crude obtained was purified by preparative reversed-phase HPLC (System 2) to give the title compound (34%).

Workup

  1. customThe mixture was placed in a sealed vessel
  2. customThe solvent was removed under reduced pressure
  3. customthe crude obtained
  4. customwas purified by preparative reversed-phase HPLC (System 2)

Sources & evidence

ORD record
ord-83b90a0eb9cc487699661ba8bbf94033
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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