3-[2-(4-Fluorophenyl)-1,3-dioxolan-2-yl]-1-propanamine → HCID 13083942, compound

HRID 1902843Notes

Reaction equation

HRID 1902843 reaction equation
[C:1]1(=[O:8])[CH:7]=[CH:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([CH2:21][CH2:22][CH2:23][NH2:24])[O:20][CH2:19][CH2:18][O:17]2)=[CH:12][CH:11]=1>CO>[F:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2([CH2:21][CH2:22][CH2:23][N:24]3[CH:6]4[CH2:5][CH2:4][CH:3]3[CH2:2][C:1](=[O:8])[CH2:7]4)[O:17][CH2:18][CH2:19][O:20]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 64515393-[2-(4-Fluorophenyl)-1,3-dioxolan-2-yl]-1-propanamineHCID 109204632,6-Cycloheptadien-1-one

Product 1

HCID 13083942HCID 13083942, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a flask equipped with a nitrogen gas inlet, addition funnel and magnetic stirrer is charged 2.7 g. (0.025 mol) of 2,6-cycloheptadienone and 90 ml. of methanol. The solution is stirred and 5.63 g. (0.025 mol) of 2-(4-fluorophenyl)-1,3-dioxolane-2-propanamine in 90 ml. of methanol is added over 30 minutes. After the addition, the reaction is allowed to stir for 20 hrs. The solution is then concentrated in vacuo to afford an oil. Chromatography on 500 g. of silica gel gives, after evaporation of solvent, 8-{3-[2-(4-fluorophenyl)1,3-dioxolan-2-yl]-propyl}-8-azabicyclo-[3.2.1]octan-3-one as an oil.

Workup

  1. customTo a flask equipped with a nitrogen gas inlet, addition funnel and magnetic stirrer
  2. additionis charged 2.7 g
  3. additionAfter the addition
  4. stirringto stir for 20 hrs
  5. concentrationThe solution is then concentrated in vacuo
  6. customto afford an oil
  7. customof silica gel gives
  8. customafter evaporation of solvent, 8-{3-[2-(4-fluorophenyl)1,3-dioxolan-2-yl]-propyl}-8-azabicyclo-[3.2.1]octan-3-one as an oil

Sources & evidence

ORD record
ord-3851e41f228a416a9ddb4541fb9a7482
Source dataset
uspto-grants-1982_12
Patent number
US04366154

Reaction notes

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