Methylamine → HCID 23594251, compound

HRID 1612408Notes

Reaction equation

HRID 1612408 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11]Br)=[CH:7][CH:6]=1.CN.[CH2:16]([N:18](CC)CC)C>O1CCCC1>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:18][CH3:16])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 11770640Methyl 2-(4-(bromomethyl)phenyl)acetate

Product 1

HCID 23594251HCID 23594251, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 15 in tetrahydrofuran (0.4 M) at room temperature under nitrogen was added methylamine (7.5 eq) and triethylamine (12.0 eq). The reaction was stirred at room temperature overnight. The tetrahydrofuran was removed under reduced pressure and the resulting oil was diluted with H2O. The aqueous layer was acidified with 6N hydrochloric acid, extracted with ethyl acetate (3×), made basic with saturated sodium bicarbonate and extracted with dichloromethane (3×). The dichloromethane was dried over sodium sulfate, filtered and concentrated in vacuo to afford the product. (66%) 1H NMR (400 MHz, CDCl3) δ 7.31 (d, 2H), 7.25 (d, 2H), 3.77 (s, 2H), 3.69 (s, 3H), 3.62 (s, 2H), 2.45 (s, 3H).

Workup

  1. customThe tetrahydrofuran was removed under reduced pressure
  2. additionthe resulting oil was diluted with H2O
  3. extractionextracted with ethyl acetate (3×)
  4. extractionextracted with dichloromethane (3×)
  5. dry with materialThe dichloromethane was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford the product

Sources & evidence

ORD record
ord-c071190051cc4e09aa2bdb0f7aa21a38
Source dataset
uspto-grants-2006_01
Patent number
US06992193B2

Reaction notes

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