2-Chloro-4-fluorobenzoyl chloride → HCID 58997314, compound

HRID 1716927Notes

Reaction equation

HRID 1716927 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:17])[CH:5]=[C:6]([N:8]([CH3:16])[CH:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[CH:7]=1.[Cl:18][C:19]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22]>O1CCOCC1>[Cl:18][C:19]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:20]=1[C:21]([NH:17][C:4]1[CH:5]=[C:6]([N:8]([CH3:16])[CH:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]2)[CH:7]=[C:2]([F:1])[CH:3]=1)=[O:22]

Participants

4

Reactant 2

HCID 27365462-Chloro-4-fluorobenzoyl chlorideHCID 58997309HCID 58997309, compound

Product 1

HCID 58997314HCID 58997314, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Combine 5-fluoro-N-methyl-N-(1-methyl-piperidin-4-yl)-benzene-1,3-diamine (Preparation 29, 0.036 g, 0.15 mmol), 2-chloro-4-fluoro-benzoyl chloride (0.044 g, 0.23 mmol) and 1,4-dioxane (2 mL), stir and heat at reflux. After 3 hr, cool to ambient temperature. Load on a SCX column (10 g), wash with methanol, elute with 2M ammonia-methanol. Concentrate eluent to obtain 0.059 g (100%) the title compound as a free base. Dissolve this material in dichloromethane (5 mL) and treat with 1M hydrochloric acid in ether (0.15 mL, 0.15 mmol). Concentrate to give the title compound as a brown powder: high resolution mass spectrum: Obs. m/z 394.1495; Calc. m/z 394.1497; 1H NMR (CDCl3) of free base: 7.8 (bs, 1H), 7.7 (m, 1H), 7.2 (m, 1H), 7.1 (m, 1H), 6.8 (s, 1H), 6.7 (m, 1H), 6.2 (m, 1H), 3.5 (m, 1H), 2.9 (m, 2H), 2.8 (s, 3H), 2.3 (s, 3H), 2.1 (m, 2H), 1.9 (m, 2H), 1.7 (m, 2H).

Workup

  1. temperatureheat
  2. temperatureat reflux
  3. washLoad on a SCX column (10 g), wash with methanol
  4. washelute with 2M ammonia-methanol

Sources & evidence

ORD record
ord-3e5bed7f463f46cd9ee54c079cd296b6
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Reaction notes

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