Hexamethylphosphoramide → HCID 86604124, compound

HRID 747273Notes

Reaction equation

HRID 747273 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][CH2:9][C:10]#[N:11])=[CH:3][CH:2]=1.CN(C)P(N(C)C)(N(C)C)=O.C([N-]C(C)C)(C)C.[Li+].Cl[CH:38]([C:40]1[CH:49]=[CH:48][CH:47]=[C:46]2[C:41]=1[CH:42]=[CH:43][CH:44]=[N:45]2)[CH3:39]>C1COCC1.CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C>[C:7](=[N:8][CH:9]([CH:38]([C:40]1[CH:49]=[CH:48][CH:47]=[C:46]2[C:41]=1[CH:42]=[CH:43][CH:44]=[N:45]2)[CH3:39])[C:10]#[N:11])([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 12679HexamethylphosphoramideHCID 612957[(Diphenylmethylene)amino]acetonitrileHCID 2724682Lithium diisopropylamideHCID 597495555-(1-Chloroethyl)quinoline2×

Product 1

HCID 86604124HCID 86604124, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 22742125Tetrahydrofuran heptane ethylbenzolSolvent

Procedure

A solution of N-(diphenylmethylene)aminoacetonitrile (5.84 g, 26.0 mmol, commercially available from Aldrich) in THF (20 mL) and hexamethylphosphoramide (HMPA) (5.43 mL, 31 mmol) at −78° C. was reacted with lithium diisopropylamide (LDA) (15.4 mL of a 2M soln in heptane/THF/ethylbenzene) (commercially available from Aldrich). After 1 h, 5-(1-chloro-ethyl)-quinoline (Intermediate E1) (4.15 g, 21.7 mmol) in THF (15 mL) was introduced by dropwise addition. The mixture was kept at −78° C. for 5 m before removal of the cold bath. After 5 m, the mixture was quenched with cold water and extracted with ethyl acetate (3×). The organic solution was dried over MgSO4, filtered and concentrated to give 2-(benzhydrylidene-amino)-3-quinolin-5-yl-butyronitrile that was used in the next step without further purification.

Workup

  1. customThe mixture was kept at −78° C. for 5 m before removal of the cold bath
  2. customAfter 5 m, the mixture was quenched with cold water
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-16db826079074b6a87ee301fc69577d0
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

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