Triethylamine → HCID 22799988, compound

HRID 1438733Notes

Reaction equation

HRID 1438733 reaction equation
Cl.[Cl:2][C:3]1[CH:27]=[CH:26][C:6]2[O:7][C@H:8]([C:17]([NH:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[O:18])[O:9][C@@H:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:5]=2[CH:4]=1.C(N(CC)CC)C>CCO.[Pd]>[ClH:2].[C:11]1([C@H:10]2[C:5]3[CH:4]=[CH:3][CH:27]=[CH:26][C:6]=3[O:7][C@H:8]([C:17]([NH:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:24])[CH3:25])=[O:18])[O:9]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 22799995HCID 22799995, compound

Product 1

HCID 22799988HCID 22799988, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

trans-6-Chloro-4-phenyl-N-(3-dimethylaminopropyl)1,3-benzodioxan-2-carboxamide hydrochloride (1.0 g., 2.43 mmole) was mixed with triethylamine (0.526 g., 5.2 mmole) and 30% Pd on Celite catalyst (0.3 g.,) in 200 ml of absolute EtOH and hydrogenated in a Parr apparatus for 30 mins. at an initial H2 pressure of 48 psi. The uptake was 13 lbs. of H2 and after catalyst removal, the filtrate was stripped of solvent under reduced pressure. The residue was partitioned between CH2Cl2 and 2% Na2CO3 solution. After extraction of the aqueous with a second portion of CH2Cl2, the organics were combined, washed with H2O, dried (MgSO4) and stripped to a syrup under reduced pressure. The .HCL salt was formed in CH2Cl2 in the usual manner, and after solvent removal, crystallization was effected by trituration in hot EtOAc, followed by cooling (0.66 g., 72%). Recrystallization from EtOAc-abs EtOH gave analytical material (mp 165°-170° d).

Workup

  1. customof H2 and after catalyst removal
  2. customThe residue was partitioned between CH2Cl2 and 2% Na2CO3 solution
  3. extractionAfter extraction of the aqueous with a second portion of CH2Cl2
  4. washwashed with H2O
  5. dry with materialdried (MgSO4)
  6. customThe .HCL salt was formed in CH2Cl2 in the usual manner
  7. customafter solvent removal, crystallization
  8. temperatureby cooling (0.66 g., 72%)
  9. customRecrystallization from EtOAc-abs EtOH
  10. customgave analytical material (mp 165°-170° d)

Sources & evidence

ORD record
ord-a11469a3295241b7967f2a0368a08a8e
Source dataset
uspto-grants-1977_11
Patent number
US04056540

Reaction notes

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