Dichloromethane → HCID 11114921, compound

HRID 1889663Notes

Reaction equation

HRID 1889663 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.C(Cl)Cl.[C:13]1([CH2:21][NH2:22])[CH:18]=[CH:17][C:16]([CH2:19][NH2:20])=[CH:15][CH:14]=1.[BH4-].[Na+]>C(O)(C)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:20][CH2:19][C:16]2[CH:17]=[CH:18][C:13]([CH2:21][NH:22][CH2:6][C:5]3[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:14][CH:15]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 680234-FluorobenzaldehydeHCID 683151,4-BenzenedimethanamineHCID 4311764Sodium borohydride

Product 1

HCID 11114921HCID 11114921, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 4-fluorobenzaldehyde (2.482 g, 20.00 mmol) in a mixed solvent (20 mL of methylene chloride nd 10 mL of i-propanol) at rt, was added 1,4-phenylenedimethanamine (1.362 g, 10 mmol, Aldrich). The reaction mixture was stirred at rt for 5 h. To this mixture, sodium borohydride (0.567 g, 15.0 mmol, 1.5 eq) was added, and it was stirred at rt overnight. The reaction mixture was quenched by adding 10 mL of MeOH and 10 mL of aq. NaHCO3. The reaction mixture was extracted with EtOAc (3×50 mL). The combined organic extracts were dried, concentrated and purified by ISCO system, eluting with CH2Cl2/EtOAc to give the title compound (2.45 g, 66%) as a viscous material, MS (ESI): 353.1 (M+H)+.

Workup

  1. stirringit was stirred at rt overnight
  2. customThe reaction mixture was quenched
  3. additionby adding 10 mL of MeOH and 10 mL of aq. NaHCO3
  4. extractionThe reaction mixture was extracted with EtOAc (3×50 mL)
  5. customThe combined organic extracts were dried
  6. concentrationconcentrated
  7. custompurified by ISCO system
  8. washeluting with CH2Cl2/EtOAc

Sources & evidence

ORD record
ord-fd44a949414940f4837f6ff0adf4e792
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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