Dimethylformamide → HCID 86665810, compound

HRID 2280845Notes

Reaction equation

HRID 2280845 reaction equation
[N:1]1([C:7]2[CH:20]=[CH:19][C:10]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CN(C)C=O.[C:26]1(C)C(C)=CC=C[CH:31]=1.[C-]#[C-].[Na+].[Na+]>O>[C:13]1([C:11]([C:10]2[CH:9]=[CH:8][C:7]([N:1]3[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]3)=[CH:20][CH:19]=2)([OH:12])[C:26]#[CH:31])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 1519739HCID 1519739, compoundHCID 178424223HCID 178424223, compound

Product 1

HCID 86665810HCID 86665810, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500 mL beaker was added the product from Step 3 (30 g) and anhydrous dimethylformamide (50 mL). Sodium acetylide xylene slurry (22 wt %, 90 g) was dropped to the mixture through addition funnel slowly. The reaction mixture was stirred with a glass stirring bar for 10 minutes. The mixture was poured into water (400 mL). The resulting mixture was extracted with ethyl acetate (200 mL). The recovered top layer was filtered through a silica gel plug using ethyl acetate and methanol mixture as eluent. Solid product was obtained by recrystallization from condensed major fraction. The solid was filtered off and dried in vacuum oven at 60° C. for 3 hours to afford 17 g of 1-phenyl-1-(4-piperazinophenyl)-2-propyn-1-ol.

Workup

  1. stirringstirring bar for 10 minutes
  2. extractionThe resulting mixture was extracted with ethyl acetate (200 mL)
  3. filtrationThe recovered top layer was filtered through a silica gel plug
  4. customSolid product was obtained by recrystallization from condensed major fraction
  5. filtrationThe solid was filtered off
  6. customdried in vacuum oven at 60° C. for 3 hours

Sources & evidence

ORD record
ord-c37de24b4aba4c11aaee0a70dd9984e7
Source dataset
uspto-grants-2015_09
Patent number
US09139552B2

Reaction notes

Loading…