Sodium Hydroxide → HCID 25195162, compound

HRID 1714029Notes

Reaction equation

HRID 1714029 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:31]([O:33]C)=[O:32])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH2:18][C:17]4[CH:27]=[CH:28][CH:29]=[CH:30][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:31]([OH:33])=[O:32])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH2:18][C:17]4[CH:27]=[CH:28][CH:29]=[CH:30][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68506576HCID 68506576, compound

Product 1

HCID 25195162HCID 25195162, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 14-cyclohexyl-6-[2-(dimethylamino)ethyl]-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate (0.16 M, 1 eq, from Step 4) in MeOH and 1N NaOH (4 eq) was heated to 80° C. for 6 h. After cooling to RT, the MeOH was removed under reduced pressure and the resulting aqueous solution acidified with aqueous 3N HCl until pH 1-2 resulting in formation of a pale yellow precipitate. This was filtered off and dried on the filter overnight to afford the crude hydrochloride salt of the product as a yellow solid. Purification was by RP-HPLC (stationary phase: column Waters XTERRA prep. MS C18, 5 μm, 30×100 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA). Fractions containing the pure compound were combined and freeze dried (2×) in the presence of 3N aqueous HCl to afford the bis-HCl salt of the title compound as a white powder (65% over steps 3, 4 and 5).

Workup

  1. customthe MeOH was removed under reduced pressure
  2. customresulting in formation of a pale yellow precipitate
  3. filtrationThis was filtered off
  4. customdried on the filter overnight

Sources & evidence

ORD record
ord-d273b38abd1041cc9f63505f2eabf423
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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