1-Indanone → 1-(1H-Inden-3-yl)pyrrolidine

HRID 1387661Notes

Reaction equation

HRID 1387661 reaction equation
[C:1]1(=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:2]1

Participants

3

Reactant 2

HCID 67351-IndanoneHCID 31268Pyrrolidine

Product 1

HCID 6039341-(1H-Inden-3-yl)pyrrolidine

Procedure

According to a modification of the procedure of Noland et al (Noland, W. E.; Kaneswaran, V. J. Org. Chem. 1981, 46, 1940-1944.), 1-indanone (25.0 g, 0.189 mol) and 50 mL of pyrrolidine which had been dried over 3A sieves were added to a 500 mL, 3-neck flask equipped with an overhead stirrer, Dean-Stark apparatus and condenser which was maintained under a dry N2 atmosphere. Benzene (200 mL dried over 4A sieves) was added and the solution was brought to reflux for 30 hours. At the end of this period 1H NMR analysis of a reaction aliquot indicated a 93:7 mole percent ratio of desired product to starting material. The bulk of the solvent was removed in vacuo and the crude dark product was distilled (6″ Vigreaux column) to give pure enamine as a light yellow oil (24.3 g, 0.132 mol) in 70 percent yield. This compound was both air and water sensitive and was transferred to the dry box upon distillation. Capillary GC analysis indicated a hexane solution of distillate to be of 99 area percent purity: bp=125-127° C. @ 2.0 mm, bp. lit=118-120° C. @ 1 mm;

Workup

  1. dry with materialhad been dried over 3A sieves
  2. additionwere added to a 500 mL, 3-neck flask
  3. customequipped with an overhead stirrer
  4. temperatureDean-Stark apparatus and condenser which was maintained under a dry N2 atmosphere
  5. additionBenzene (200 mL dried over 4A sieves) was added
  6. temperatureto reflux for 30 hours
  7. customAt the end of this period 1H NMR analysis of a reaction

Sources & evidence

ORD record
ord-06377a66602f4d3895e91bdc591ac44f
Source dataset
uspto-grants-2001_07
Patent number
US06268444B1

Reaction notes

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