Potassium Iodide → 1-(3-(12H-dibenzo[d,g]-[1,3]dioxocin-12-ylidene)-1-propyl)-3-pyrrolidineacetic acid methyl ester

HRID 1291034Notes

Reaction equation

HRID 1291034 reaction equation
Cl.[CH:2]1[C:13]2[C:12](=[CH:14][CH2:15][CH2:16][N:17]3[CH2:21][CH2:20][CH:19]([CH2:22][C:23]([OH:25])=[O:24])[CH2:18]3)[C:11]3[CH:26]=[CH:27][CH:28]=[CH:29][C:10]=3[O:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.Br[CH2:31]CC=C1C2C=CC=CC=2OCOC2C=CC=CC1=2.C(O)(=O)C.N1CCC(CC(OC)=O)C1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC.CCOCC.O>[CH3:31][O:24][C:23](=[O:25])[CH2:22][CH:19]1[CH2:20][CH2:21][N:17]([CH2:16][CH2:15][CH:14]=[C:12]2[C:11]3[CH:26]=[CH:27][CH:28]=[CH:29][C:10]=3[O:9][CH2:8][O:7][C:6]3[CH:5]=[CH:4][CH:3]=[CH:2][C:13]2=3)[CH2:18]1

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 17127115-(3-Bromopropylidene)benzo[d][1,3]benzodioxocineHCID 70009063Methyl 3-pyrrolidineacetate acetateHCID 701006231-(3-(12H-Dibenzo[d,g][1,3]dioxocin-12-ylidene)-1-propyl)-3-pyrrolidineacetic acid hydrochloride

Product 1

HCID 701033121-(3-(12H-dibenzo[d,g]-[1,3]dioxocin-12-ylidene)-1-propyl)-3-pyrrolidineacetic acid methyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

1-(3-(12H-Dibenzo[d,g][1,3]dioxocin-12-ylidene)-1-propyl)-3-pyrrolidineacetic acid hydrochloride ##STR8## A mixture of 12-(3-bromo-1-propylidene)-12H-dibenzo[d,g][1,3]dioxocine (500 g, 15 mmol, prepared as described in example 1), methyl 3-pyrrolidineacetate acetate (3.04 g, 15 mmol), potassium carbonate (6.2 g, 45 mmol) and potassium iodide (2.23 g, 13 mmol) in 2-butanone (70 ml) was heated at reflux temperature for 5 h. The readon mixture was cooled and water (140 ml) and ether (140 ml) were added. The mixture was vigorously stirred for 5 minutes, the organic layer was separated, washed with water (2×50 ml) and dried over MgSO4. The solvent was evaporated in vacuo and the residue (4.34 g) was submitted to column chromatography on silica gel (100 g) using a mixture of dichloro-methane and methanol (10:1) as eluent. This afforded l.05 g of 1-(3-(12H-dibenzo[d,g]-[1,3]dioxocin-12-ylidene)-1-propyl)-3-pyrrolidineacetic acid methyl ester.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 5 h
  3. temperatureThe readon mixture was cooled
  4. customthe organic layer was separated
  5. washwashed with water (2×50 ml)
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated in vacuo
  8. additiona mixture of dichloro-methane and methanol (10:1) as eluent

Sources & evidence

ORD record
ord-db09788d7f184055b2cf04c3d3a5f1b9
Source dataset
uspto-grants-1998_05
Patent number
US05753678

Reaction notes

Loading…