Hydrochloric Acid → HCID 58916994, compound

HRID 600242Notes

Reaction equation

HRID 600242 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.[CH:13]1([NH2:18])[CH2:17][CH2:16][CH2:15][CH2:14]1.CC1C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+].Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([NH:18][CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:6][CH2:5]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2906CyclopentylamineHCID 6101p-Toluenesulfonic acidHCID 27335536-Bromo-2-tetraloneHCID 4311764Sodium borohydride

Product 1

HCID 58916994HCID 58916994, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Charged 50 mL round bottomed flask with 6-bromo-2-tetralone (0.750 g., 3.33 mmoles., 1.0 eq.), cylcopentylamine (0.567 g., 0.648 mL., 6.66 mmoles., 2.0 eq.) and catalytic amount of tosic acid. Fitted flask with a Dean-Stark trap and heated reaction mixture overnight at 155° C. The next day, removed remaining solvent from reaction mixture using reduced pressure. Added 25 mL of methanol and placed reaction mixture on an ice bath. Added sodium borohydride (0.630 g, 16.6 mmoles, 5.0 eq.). Removed ice bath and allowed to stir for several hours. Partitioned reaction mixture between ethyl acetate and 1.0 N HCl aqueous solution. Extracted organic layer two times more with 1.0 N HCl solution. Combined acidic extractions and basified with 5.0 N NaOH. Extracted basic aqueous with methylene chloride three times. Combined organic extracts and dried over Na2SO4. Removed solvents using reduced pressure to obtain 0.429 g. (crude yield=43%). Purified using a reverse phase column and acetonitrile:TFA buffer solvent gradient. Collected TFA salt of 6-bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-cyclopentyl-amine. Partitioned the product between methylene chloride and 2.0N sodium carbonate solution. Washed organic layer with 2.0N sodium carbonate a second time and then with brine. Dried organic layer over sodium sulfate and removed solvent via reduced pressure to obtain 0.324 g. (yield=33%). Mass spectrum (APCI): 294 (M++1).

Workup

  1. customFitted flask with a Dean-Stark trap
  2. temperatureheated
  3. customreaction mixture overnight at 155° C
  4. customThe next day, removed
  5. customfrom reaction mixture
  6. customreaction mixture on an ice bath
  7. customRemoved ice bath and allowed
  8. customPartitioned
  9. customreaction mixture between ethyl acetate and 1.0 N HCl aqueous solution
  10. extractionCombined acidic extractions
  11. extractionExtracted basic aqueous with methylene chloride three times
  12. dry with materialCombined organic extracts and dried over Na2SO4
  13. customto obtain 0.429 g
  14. customPurified
  15. customPartitioned the product between methylene chloride and 2.0N sodium carbonate solution
  16. customDried organic layer over sodium sulfate and removed solvent via reduced pressure
  17. customto obtain 0.324 g

Sources & evidence

ORD record
ord-ef61ba65a5d34a26ac39f5156962e414
Source dataset
uspto-grants-2011_03
Patent number
US07902191B2

Reaction notes

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