Water → HCID 22262779, compound

HRID 489829Notes

Reaction equation

HRID 489829 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-df54537e9e714b2b84bc8a8767052c4d
Source dataset
uspto-grants-2005_12
Patent number
US06979693B2

Reaction notes

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