2-Chloro-N,N-dimethylethylamine → HCID 21873312, compound

HRID 723360Notes

Reaction equation

HRID 723360 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)[C:9]2=[O:28])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:31][N:32]([CH3:36])[CH2:33][CH2:34]Cl>C1COCC1.O>[CH3:31][N:32]([CH3:36])[CH2:33][CH2:34][O:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[CH:17][CH:16]=3)[C:9]2=[O:28])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 21873463HCID 21873463, compound

Product 1

HCID 21873312HCID 21873312, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(4-hydroxyphenyl)-3-(4-phenoxyphenyl)-[1,3]-diazepan-2-one (26 mg) was dissolved in THF (2 mL), and sodium hydride (80% in oil, 3 mg) was added. After 30 minutes, 2-dimethylaminoethyl chloride (hydrochloride, 11 mg) was added. After 16 hours, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried and concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 445.57 (C27H31 N3O3); MS (ESI): 446 ([M+H]+), was obtained in this way.

Workup

  1. waitAfter 16 hours
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC
  6. customMS (ESI): 446 ([M+H]+), was obtained in this way

Sources & evidence

ORD record
ord-d580c6c9b4ca484fa01b37157d543d78
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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