Lithium diisopropylamide → HCID 13500289, compound

HRID 371183Notes

Reaction equation

HRID 371183 reaction equation
[CH:1]([N-:4]C(C)C)(C)C.[Li+].[CH2:9]1[C:22]2[CH:13]([NH:14][CH:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH2:16]3)[CH2:12][CH2:11][CH2:10]1.C(N(C1CCCCC1)C#N)(C)(C)C>O1CCCC1>[C:1]([CH:12]1[C:13]2[C:22](=[CH:21][C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[N:14]=2)[CH2:9][CH2:10][CH2:11]1)#[N:4]

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 13500287HCID 13500287, compoundHCID 23065677HCID 23065677, compound

Product 1

HCID 13500289HCID 13500289, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium diisopropylamide [ex 1.55M BuLi/hexane (32.3 ml, 50 mM), diisopropylamine (3.5 ml, 25 mM), tetrahydrofuran (20 ml)] maintained at 0° C. under an argon atmosphere was treated with a solution of octahydroacridine (4.68 g, 25 mM) in the tetrahydrofuran (10 ml). After 0.5 hours a solution of N-t-butyl-N-cyclohexylcyanamide (4.6 g, 28 mM) in tetrahydrofuran (10 ml) was added and the mixture stirred overnight. The reaction was quenched with water, extracted with toluene and the organic phase washed with water, dried and evaporated. The residue, dissolved in ethyl acetate, was passed through a short silica column to yield the title compound. (3.8 g) mp. 88°-90° C.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with toluene
  3. washthe organic phase washed with water
  4. customdried
  5. customevaporated
  6. dissolutionThe residue, dissolved in ethyl acetate

Sources & evidence

ORD record
ord-ac21dda39d694a058d96b2c38527d3aa
Source dataset
uspto-grants-1985_07
Patent number
US04529798

Reaction notes

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