Triethylamine → HCID 22799972, compound

HRID 1438735Notes

Reaction equation

HRID 1438735 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 22799977HCID 22799977, compound

Product 1

HCID 22799972HCID 22799972, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

cis-6-Chloro-4-phenyl-N-(3-dimethylaminopropyl)-1,3-benzodioxan-2-carboxamide hydrochloride (1.06 g, 2.59 mmole), triethylamine (0.526 g., 5.2 mmole) and 30% Pd on Celite (0.6 g) were mixed in abs EtOH (200 ml) and hydrogenated in a Parr apparatus for 21/2 hrs. (14 lb H2 uptake). Workup and treatment with HClg in the usual manner (see example 12) gave the product (0.7 g., 71.8% mp 178°-186° d) after recrystallization from i-PrOH:Et2O.

Workup

  1. customWorkup and treatment with HClg in the usual manner (see example 12) gave the product (0.7 g., 71.8% mp 178°-186° d)
  2. customafter recrystallization from i-PrOH

Sources & evidence

ORD record
ord-5e9ed4b78c764c5984f9a47182898228
Source dataset
uspto-grants-1977_11
Patent number
US04056540

Reaction notes

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