Triphosgene → 1,2,3,5,6,7-Hexahydro-s-indacene

HRID 1276543Notes

Reaction equation

HRID 1276543 reaction equation
[CH2:1]1[C:12]2[C:4](=[C:5](N)[C:6]3[CH2:7][CH2:8][CH2:9][C:10]=3[CH:11]=2)[CH2:3][CH2:2]1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1.C(N(CC)CC)C>[CH2:3]1[C:4]2[C:12](=[CH:11][C:10]3[CH2:9][CH2:8][CH2:7][C:6]=3[CH:5]=2)[CH2:1][CH2:2]1

Participants

5

Reactant 2

HCID 94429TriphosgeneHCID 112522851,2,3,5,6,7-Hexahydro-s-indacen-4-amine

Product 1

HCID 1363211,2,3,5,6,7-Hexahydro-s-indaceneYield 113.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 1,2,3,5,6,7-hexahydro-s-indacen-4-ylamine (77 grams) in tetrahydrofuran (1.5 L) and triethylamine (68.3 mL) was added triphosgene (43.9 grams) in one portion. The mixture was heated to reflux for 1/2 hour, then cooled to room temperature. The tetrahydrofuran was removed under reduced pressure, and the residue was taken up in pentane and filtered through a plug of silica gel. Removal of the pentane in vacuo afforded 80 grams of a white solid, m.p. 35.0-36.2° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1/2 hour
  3. customThe tetrahydrofuran was removed under reduced pressure
  4. filtrationfiltered through a plug of silica gel
  5. customRemoval of the pentane in vacuo

Sources & evidence

ORD record
ord-54990c22b84c4440ad921ae24b416eea
Source dataset
uspto-grants-2000_12
Patent number
US06166064

Reaction notes

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