Propylamine → [(2,4-Difluorophenyl)methyl](propyl)amine

HRID 899892Notes

Reaction equation

HRID 899892 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C(OC)(OC)OC.[CH2:18]([NH2:21])[CH2:19][CH3:20].[BH4-]>CO.C(Cl)Cl.C(O)(=O)C>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH:21][CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 4

HCID 7852PropylamineHCID 9005Trimethyl orthoformateHCID 28123BorohydrideHCID 737702,4-Difluorobenzaldehyde

Product 1

HCID 24690356[(2,4-Difluorophenyl)methyl](propyl)amineYield 71%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2,4-Difluorbenzaldehyde (1.003 g, 7.055 mmol) was dissolved in methanol (5 ml). Trimethyl orthoformate (5 ml) was added. Propylamine (401 mg, 6.784 mmol) was then added and followed by acetic acid (0.2 ml). After 1 hour, DCM (5 ml) was added and followed by borohydride polymer-supported (2.5 mmol/g, 5.42 g, 13.55 mmol). The mixture was shaken at room temperature for 4 days and then filtered. The filtrate was evaporated. The residue was dissolved in acetonitrile, then divided into two portions and loaded on two columns (ISOLUTE®PRS, 10 g/70 ml, wetted with acetonitrile). It was eluted with acetonitrile, then methanol and then methanol (NH3 sat.). The product fractions were combined and evaporated. Oil product (892 mg) was obtained, yield 71%.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. dissolutionThe residue was dissolved in acetonitrile
  4. washIt was eluted with acetonitrile
  5. customevaporated

Sources & evidence

ORD record
ord-c571e9a2c4f54b998eeed8db068ed642
Source dataset
uspto-grants-2008_04
Patent number
US07355069B2

Reaction notes

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