Potassium Carbonate → HCID 66726848, compound

HRID 2407251Notes

Reaction equation

HRID 2407251 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[CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([C:18]2[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=2)[CH2:13]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:32][CH2:33][CH2:34][OH:35]>CC#N>[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[CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([C:18]2[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=2)[O:24][CH2:32][CH2:33][CH2:34][OH:35])[CH2:13]1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 123083-Bromo-1-propanol2×HCID 251750011106938-11-7

Product 1

HCID 66726848HCID 66726848, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R*)-3-{1-[(S)-1-(2,3-Dihydrobenzo[1,4]dioxin-2-yl)methyl]piperidin-3-yl}phenol (208 mg, 0.64 mmol), K2CO3 (103 mg, 0.74 mmol), 3-bromo-1-propanol (86 mg, 0.62 mmol) and MeCN (5 ml) were heated under microwaves at 105° C. for 6 h. More K2CO3 (103 mg) and 3-bromo-1-propanol (86 mg) were added and the heating was continued for 2 h. The solvent was removed and the residue was taken up in DCM. This solution was washed with water and 1 M NaOH and evaporated to dryness. Flash chromatography (heptane/EtOAc) gave 76 mg of the title compound.

Workup

  1. customThe solvent was removed
  2. washThis solution was washed with water and 1 M NaOH
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-7a8abb34528f45b68191ec2491227712
Source dataset
uspto-grants-2014_08
Patent number
US08809536B2

Reaction notes

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