Pyrrolidine → HCID 12017560, compound

HRID 2303375Notes

Reaction equation

HRID 2303375 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]Br)=[CH:24][CH:23]=2)=[O:21])=[CH:5][CH:4]=1.[NH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][N:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)=[CH:24][CH:23]=2)=[O:21])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 12017554HCID 12017554, compound

Product 1

HCID 12017560HCID 12017560, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1280 mg (2.2 mmol) of [2-(4-Methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-(8-bromo-octyloxy)phenyl]methanone and 470 mg (6.6 mmol) of pyrrolidine were dissolve in 20 mL of dimethylformamide (DMF). The reaction mixture was heated to 100° C. and stirred under a nitrogen atmosphere. After 30 minutes, the reaction was allowed to cool and evaporated to dryness in vacuo. The crude product was chromatographed on a silica gel column eluted with a linear gradient begining with CHCl3 and ending with CHCl3—MeOH (19:1) (v/v). The desired fractions were determined by tlc, combined, and evaporated to dryness. This yielded 890 mg (72%) of the title compound as a tan, amorphous powder.

Workup

  1. temperatureto cool
  2. customevaporated to dryness in vacuo
  3. customThe crude product was chromatographed on a silica gel column
  4. washeluted with a linear gradient
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-9d61d6caceff4a67b05193b442fa7204
Source dataset
uspto-grants-2002_08
Patent number
US06432983B1

Reaction notes

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