Pyrrolidine → HCID 22641327, compound

HRID 2415496Notes

Reaction equation

HRID 2415496 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[CH:14][C:15]([CH3:19])=[N:16]2)=[CH:11][C:10]=1[F:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:14][C:15]([CH3:19])=[N:16]2)=[CH:11][C:10]=1[F:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 22641319HCID 22641319, compound

Product 1

HCID 22641327HCID 22641327, compoundYield 46.4%

Conditions

Temperature
80 °C

Procedure

A mixture of 3.1 g of (10.9 mmol) of 7-benzyloxy-4-chloro-6-fluoro-2-methyl-quinoline and 18.1 ml (21.8 mmol) pyrrolidine was heated at 80° C. (oil bath temperature) under an argon atmosphere for 6 h. The reaction mixture was concentrated in vacuo, the residue taken up in methylene chloride, which was washed with water, saturated NaCl solution and then dried over magnesium sulphate. The solvent was removed in vacuo, the residue purified by flash chromatography on silica gel with CH2Cl2/MeOH (100:0 to 90:10 over 1 h) as eluent. Combination of the purified fractions and concentration in vacuo gave 1.7 g (46.2%) of the 7-benzyloxy-6-fluoro-2-methyl-4-pyrrolidin-1-yl-quinoline as a brown crystalline solid. ISP mass spectrum, m/e: 337.4 (M+1 calculated for C21H21FN2O: 337).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwhich was washed with water, saturated NaCl solution
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was removed in vacuo
  5. customthe residue purified by flash chromatography on silica gel with CH2Cl2/MeOH (100:0 to 90:10 over 1 h) as eluent
  6. concentrationCombination of the purified fractions and concentration in vacuo

Sources & evidence

ORD record
ord-80622d96e3124d8096a8a69533ad1069
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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