Diisopropylethylamine → Indane

HRID 1253745Notes

Reaction equation

HRID 1253745 reaction equation
O.ON1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2N=N1.C(N(C(C)C)[CH:15]([CH3:17])[CH3:16])C.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH2:16]1[C:7]2[C:6](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:17][CH2:15]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 10326Indane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-Hydroxybenzotriazole hydrate (0.3 eq.) and N-ethyl-diisopropylamine (4 eq.) were added to a solution of (G) (1.5 eq.) in methylene chloride. The reaction mixture was cooled to 0° C. and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.5 eq.) was then added. The mixture was stirred at this temperature for 15 min, before the amine (1 eq.) was finally added. The reaction mixture was then stirred at room temperature overnight. For working up, the reaction mixture was washed 3× with 0.5 M KOH solution and the organic phase was dried over MgSO4, filtered and concentrated. The crude product was either purified by column chromatography (silica; methylene chloride/methanol or aluminium oxide; methylene chloride/methanol) or recrystallized from methylene chloride to obtain the product (H) in a pure form.

Workup

  1. additionwas finally added
  2. washthe reaction mixture was washed 3× with 0.5 M KOH solution
  3. dry with materialthe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was either purified by column chromatography (silica; methylene chloride/methanol or aluminium oxide; methylene chloride/methanol)
  7. customrecrystallized from methylene chloride

Sources & evidence

ORD record
ord-a00a8ae69f544abba677df0012d9eec5
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

Loading…