Water → HCID 22262779, compound

HRID 429354Notes

Reaction equation

HRID 429354 reaction equation
[CH:1]([N-:4]C(C)C)(C)C.[Li+].C(#N)C.[N:12]1([CH2:18][CH2:19][O:20][C:21]2[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=2)[C:24](OC)=O)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.O>O1CCCC1>[N:12]1([CH2:18][CH2:19][O:20][C:21]2[CH:22]=[C:23]([CH2:24][C:1]#[N:4])[CH:28]=[CH:29][CH:30]=2)[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 2724682Lithium diisopropylamideHCID 7164628Methyl 3-(2-morpholin-4-ylethoxy)benzoate

Product 1

HCID 22262779HCID 22262779, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium diisopropylamide (18.8 ml, 37 mmol, 2.0 M solution in heptane/tetrahydrofuran/ethylbenzene) was added dropwise to a solution of acetonitrile (1.58 g, 37 mmol) in dry tetrahydrofuran (50 ml) at −78° C. After stirring the reaction mixture for 30 min., a solution of methyl 3-(2-morpholin-4-ylethoxy)benzoate in dry tetrahydrofuran (50 ml) was added dropwise over 10 min. After 15 min., water was added and the reaction mixture was allowed to warm to room temperature. The aqueous layer was separated and acidified with dilute hydrochloric acid to pH 7. The product was extracted into ethyl acetate and washed with water and brine and dried over magnesium sulfate. The organics were removed in vacuo to give 2-[3-(2-morpholin-4-ylethoxy)phenyl]acetonitrile (5.0 g) as an oil which was used in the next step without further purification.

Workup

  1. waitAfter 15 min.
  2. customThe aqueous layer was separated
  3. extractionThe product was extracted into ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe organics were removed in vacuo

Sources & evidence

ORD record
ord-21f71b6700054f2a84c7fe8723f78386
Source dataset
uspto-grants-2001_11
Patent number
US06316466B1

Reaction notes

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