Dimethylformamide → HCID 59640447, compound

HRID 2250143Notes

Reaction equation

HRID 2250143 reaction equation
CN(C=O)C.Br[CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:26]=[CH:25][C:15]([CH2:16][NH:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:14][CH:13]=1.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(Cl)Cl>[N:27]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:26]=[CH:25][C:15]([CH2:16][NH:17][CH2:18][CH2:19][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:14][CH:13]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8082PiperidineHCID 69311104HCID 69311104, compound

Product 1

HCID 59640447HCID 59640447, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An 8 mL DMF solution of [4-(4-bromo-butoxy)-benzyl]-(2-pyrrolidin-1-yl-ethyl)-amine (307 mg, 0.86 mmol) and piperidine (0.22 mL, 2.2 mmol) is stirred at 90° C. for six hours under N2. The reaction mixture is cooled, diluted with CH2Cl2, filtered, washed with brine, dried (Na2SO4), and concentrated. The residue is purified by chromatography (SiO2; 0-6% MeOH/CH2Cl2/1% NH4OH gradient) to give the product (40 mg, 12% yld). MS(ES+)360.4(M+H)+ free base.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography (SiO2; 0-6% MeOH/CH2Cl2/1% NH4OH gradient)
  7. customto give the product (40 mg, 12% yld)

Sources & evidence

ORD record
ord-8f8bf6d69ac1496d8c61d32df75e1876
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

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