HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Thionyl Chloride → 3-Benzo[1,3]dioxol-5-ylpiperidin-1-yl-(R)-2,3-dihydrobenzo[1,4]dioxin-2-ylmethanone

HRID 453761
Notes
Print preview

Reaction equation

HRID 453761 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[C:11]([OH:13])=O.S(Cl)(Cl)=O.Cl.[O:19]1[C:23]2[CH:24]=[CH:25][C:26]([CH:28]3[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]3)=[CH:27][C:22]=2[O:21][CH2:20]1.CCN(C(C)C)C(C)C>C(Cl)Cl.O.C1(C)C=CC=CC=1>[O:19]1[C:23]2[CH:24]=[CH:25][C:26]([CH:28]3[CH2:33][CH2:32][CH2:31][N:30]([C:11]([C@@H:2]4[O:1][C:6]5[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=5[O:4][CH2:3]4)=[O:13])[CH2:29]3)=[CH:27][C:22]=2[O:21][CH2:20]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 687062(R)-1,4-Benzodioxane-2-carboxylic acidHCID 667274853-benzo[1,3]dioxol-5-yl-piperidine HCl

Product 1

HCID 667272583-Benzo[1,3]dioxol-5-ylpiperidin-1-yl-(R)-2,3-dihydrobenzo[1,4]dioxin-2-ylmethanoneYield 84.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of (R)-2,3-dihydrobenzo[1,4]dioxine-2-carboxylic acid (167 mg, 0.93 mmol), thionyl chloride (338 μl, 551 mg, 4.63 mmol) and dry toluene was heated at 95° C. for 1.5 h and then evaporated to dryness. Toluene was added and the evaporation was repeated. The evaporation residue was dissolved in DCM (2 ml) and added slowly to a cold solution (0° C.) of 3-benzo[1,3]dioxol-5-yl-piperidine HCl (224 mg, 0.93 mmol) and DIPEA (0.324 ml, 240 mg, 1.85 mmol) in DCM (5 ml). The reaction mixture was stirred for 1 h 45 min at RT. Water was added, layers were separated and the organic phase was washed twice with 1 M HCl and sat. NaHCO3. The organic phase was dried (Na2SO4), filtered and evaporated to give 290 mg of the title compound.

Workup

  1. customevaporated to dryness
  2. additionToluene was added
  3. customthe evaporation
  4. dissolutionThe evaporation residue was dissolved in DCM (2 ml)
  5. customlayers were separated
  6. washthe organic phase was washed twice with 1 M HCl and sat. NaHCO3
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-1335d4f8ec1f4b57b1c95abcea570aed
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492549B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes