Sodium Hydroxide → 7-({2-[benzyl(methyl)amino]ethoxy}methyl)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid

HRID 1669493Notes

Reaction equation

HRID 1669493 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:28]([O:30]C)=[O:29])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([CH2:26][OH:27])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[Cl-].[CH2:35]([NH+:42]([CH3:46])[CH2:43][CH2:44]Cl)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:35]([N:42]([CH3:46])[CH2:43][CH2:44][O:27][CH2:26][CH:16]1[CH2:15][N:14]2[C:13]3[CH:12]=[C:11]([C:28]([OH:30])=[O:29])[CH:10]=[CH:9][C:8]=3[C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:21]2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 31967Benzylamine, N-(2-chloroethyl)-N-methyl-, hydrochlorideHCID 66674539HCID 66674539, compound

Product 1

HCID 866279097-({2-[benzyl(methyl)amino]ethoxy}methyl)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

A solution of (+)-methyl 14-cyclohexyl-7-(hydroxymethyl)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (second eluting isomer) in toluene (0.04 M) was treated with 30% w/v NaOH (10 eq) and tetrabutylammonium bromide (0.25 eq) followed by N-benzyl-2-chloro-N-methylethanaminium chloride (prepared as described in example 7 step 1) (2.5 eq). The resulting solution was stirred at 65° C. for 18 h. Toluene was removed in vacuo, the residue was taken up in EtOAc and washed with 1N HCl (aq) and brine before drying (Na2SO4), filtering and concentrating in vacuo to afford the product as an oil that was used without further purification. (ES+) m/z 553 (M+H)+.

Workup

  1. customToluene was removed in vacuo
  2. washwashed with 1N HCl (aq) and brine
  3. dry with materialbefore drying (Na2SO4)
  4. filtrationfiltering
  5. concentrationconcentrating in vacuo

Sources & evidence

ORD record
ord-98a6c263c3fd43759dce62a44175fd1d
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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