4-Chlorobutanoic acid → HCID 19775183, compound

HRID 1613131Notes

Reaction equation

HRID 1613131 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.C1(N)C2C(=CC=CC=2)CCC1.ClCCCC(O)=O.Cl[CH2:32][CH2:33][CH2:34][C:35]([NH:37][CH:38]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:41][CH2:40][CH2:39]1)=[O:36].[H-].[Na+]>C(Cl)Cl.CC#N>[CH:38]1([N:37]2[CH2:32][CH2:33][CH2:34][C:35]2=[O:36])[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:41][CH2:40][CH2:39]1

Participants

8

Reactant 5

HCID 123004-Chlorobutanoic acidHCID 180661,2,3,4-Tetrahydro-1-naphthylamineHCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 11265230Butanamide, 4-chloro-N-(1,2,3,4-tetrahydro-1-naphthalenyl)-

Product 1

HCID 19775183HCID 19775183, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

CDI (6.61 g. 40.75 mmoles) and, after 1 hour, 1,2,3,4-tetrahydro-1-naphtylamine (5 g, 33.96 mmoles) were added to 4-chlorobutyric acid (4.16 g, 33.96 mmoles) in CH2Cl2 (200 mL) under stirring. The resulting solution was kept at room temperature for 40 hours, then washed with 1N HCl, NaHCO3 (saturated solution), H2O, NaCl (saturated solution) and dried over anhydrous Na2SO4. The solvent was evaporated and the residue taken up with CHCl3. Upon addition of Et2O under stirring a precipitate was obtained consisting of 4.5 g (17.87 mmoles) of N-(4-chloro-butyroyl)-1,2,3,4,-tetrahydro-1-naphtylamine (silica gel TLC; Eluant EtOAc-Hexane (1:1), RF=0.7) which was dissolved in CH3CN (100 mL). To the mixture, 80% NaH in mineral oil (804 mg, 26.8 mmoles) was added in two portions, the second portion after some hours following the first one. The mixture was then kept at room temperature under stirring for 2 days. The mixture was then filtered, the filtrate evaporated and the residue chromatographed on silica gel using EtOAc-Hexane (1:1) as eluant. 1.93 g of the title compound were obtained. Last step yield=50%, overall yield 26%.

Workup

  1. washwashed with 1N HCl, NaHCO3 (saturated solution), H2O, NaCl (saturated solution)
  2. dry with materialdried over anhydrous Na2SO4
  3. customThe solvent was evaporated
  4. additionUpon addition of Et2O
  5. stirringunder stirring a precipitate
  6. customwas obtained
  7. waitthe second portion after some hours following
  8. customwas then kept at room temperature
  9. stirringunder stirring for 2 days
  10. filtrationThe mixture was then filtered
  11. customthe filtrate evaporated
  12. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-108fd700b29a4d3bb2d0f99e1f5b9f72
Source dataset
uspto-grants-1993_03
Patent number
US05192759

Reaction notes

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