Benzenemethanamine, 3,4-dichloro- → HCID 58460223, compound

HRID 1946511Notes

Reaction equation

HRID 1946511 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH2:11][CH2:10][CH2:9][C:8](=O)[C:7]=1O)[CH3:2].C([O-])(=O)C.[NH4+:19].[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:24][NH2:25].[CH:30](=O)[CH:31]([CH3:33])[CH3:32]>C(Cl)(Cl)Cl.C(O)(=O)C>[Cl:20][C:21]1[CH:22]=[C:23]([CH2:24][N:25]2[C:7]3[CH:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:14])[CH2:11][CH2:10][CH2:9][C:8]=3[N:19]=[C:30]2[CH:31]([CH3:33])[CH3:32])[CH:26]=[CH:27][C:28]=1[Cl:29]

Participants

7

Reactant 4

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 6561IsobutyraldehydeHCID 517165Ammonium AcetateHCID 58460212HCID 58460212, compound

Product 1

HCID 58460223HCID 58460223, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

A solution of Intermediate 45 (600 mg), ammonium acetate (233 mg), 3,4-dichlorobenzylamine (0.484 mL), acetic acid (0.866 mL) and isobutyraldehyde (0.276 mL) in chloroform (6 mL) was heated to 65° C. The reaction was heated for 21 hr, after which time the reaction mixture was partitioned between ethyl acetate (100 mL) and 1 M NaOH aqueous soln. (100 mL). The organic layer was separated and the aqueous layer extracted with further DCM (1×100 mL). The combined organic layers were filtered through a hydrophobic frit and conc. in vacuo to afford 1.18 g of crude product. The crude product was purified by flash column chromatography (silica, 0-100% cyclohexane/ethyl acetate) to afford the desired regioisomer (250 mg). LC/MS MH+ 409/411/413, Rt 2.47 min (5 min run).

Workup

  1. temperatureThe reaction was heated for 21 hr
  2. customafter which time the reaction mixture was partitioned between ethyl acetate (100 mL) and 1 M NaOH aqueous soln
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with further DCM (1×100 mL)
  5. filtrationThe combined organic layers were filtered through a hydrophobic frit and conc. in vacuo

Sources & evidence

ORD record
ord-618220a19d9d4a83ab758cfd206ad61a
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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