Dimethylamine, hydrochloride → HCID 67047555, compound

HRID 606935Notes

Reaction equation

HRID 606935 reaction equation
C[CH2:2][N:3]=[C:4]=NCCCN(C)C.[ClH:12].C(N(C(C)C)CC)(C)C.Cl.CNC.[C:26]1([C:32]#[C:33][C:34]2[CH:35]=[N:36][CH:37]=[C:38]([CH:42]=2)[C:39](O)=[O:40])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1.C(OCC)(=O)C>[ClH:12].[CH3:2][N:3]([CH3:4])[C:39](=[O:40])[C:38]1[CH:42]=[C:34]([C:33]#[C:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:35]=[N:36][CH:37]=1

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27792365-(2-Phenyleth-1-Ynyl)Nicotinic Acid

Product 1

HCID 67047555HCID 67047555, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (0.34 g, 1.8 mmol) to a solution of diisopropylethyl amine (0.47 mg, 2.7 mmol), dimethylamine hydrochloride (0.11g, 1.34 mmol) and 5-phenylethynyl-nicotinic acid (0.2 g, 0.9 mmol) in tetrahydrofuran and stir at room temperature for 18 h. Dilute the reaction mixture with ethyl acetate and extract with an aqueous saturated solution of sodium carbonate. Extract the aqueous layer with ethyl acetate. Combine organic layers, dry (magnesium sulfate), filter and concentrate. Purify by silica gel chromatography, eluting with 40:60 to 80:20 ethyl acetate:hexanes, to give the free base of the title compound as a colorless oil. Convert the free base to the hydrochloride salt as described in EXAMPLE 163 to give the title compound (0.18 g, 69%).

Workup

  1. extractionextract with an aqueous saturated solution of sodium carbonate
  2. extractionExtract the aqueous layer with ethyl acetate
  3. dry with materialCombine organic layers, dry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify by silica gel chromatography
  7. washeluting with 40:60 to 80:20 ethyl acetate

Sources & evidence

ORD record
ord-5ebc6fbefd35431eafa2e512863a664b
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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