Potassium Carbonate → Noribogaine hydrochloride

HRID 2199275

Reaction equation

HRID 2199275 reaction equation
[CH3:1][CH2:2][C@@H:3]1[C@@H:8]2[N:9]3[CH2:11][CH2:12][C:13]4[C:17]5[CH:18]=[C:19]([O:22]C)[CH:20]=[CH:21][C:16]=5[NH:15][C:14]=4[C@@H:7]2[CH2:6][C@H:5]([CH2:10]3)[CH2:4]1.[ClH:24].[CH3:25][CH2:26][C@@H:27]1[C@@H:32]2[N:33]3[CH2:35][CH2:36][C:37]4[C:41]5[CH:42]=[C:43]([O:46]C)[CH:44]=[CH:45][C:40]=5[NH:39][C:38]=4[C@@H:31]2[CH2:30][C@@H:29]([CH2:34]3)[CH2:28]1.C(=O)([O-])[O-].[K+].[K+].CC[C@H]1C2N3CCC4C5C=C(O)C=CC=5NC=4[C@H]2CC(C3)C1.Br.B(Br)(Br)[Br:78]>C(Cl)Cl.CO>[CH3:1][CH2:2][C@H:3]1[CH:8]2[N:9]3[CH2:11][CH2:12][C:13]4[C:17]5[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:16]=5[NH:15][C:14]=4[CH:7]2[CH2:6][C@@H:5]([CH2:10]3)[CH2:4]1.[ClH:24].[CH3:25][CH2:26][C@H:27]1[CH:32]2[N:33]3[CH2:35][CH2:36][C:37]4[C:41]5[CH:42]=[C:43]([OH:46])[CH:44]=[CH:45][C:40]=5[NH:39][C:38]=4[C@H:31]2[CH2:30][CH:29]([CH2:34]3)[CH2:28]1.[BrH:78]

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 197059Ibogaine hydrochlorideHCID 44210810-Methoxyibogamine2×HCID 86685292Noribogaine hydrobromide

Product 2

HCID 321672Noribogaine hydrochlorideHCID 86685292Noribogaine hydrobromide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Alternatively, noribogaine hydrochloride was prepared from ibogaine hydrochloride by first converting it to a free base, ibogaine, by treating with methanol followed by treatment with a base such as potassium carbonate in a solvent such as methylene chloride. Ibogaine was then converted to noribogaine hydrobromide by treating with boron tribromide or other conventional demethylating agent in a solvent such as methylene chloride followed by quenching with methanol to give noribogaine hydrobromide. Noribogaine hydrobromide was then converted to the free base by treating with a base such as potassium carbonate in a solvent such as methylene chloride, followed by purification over silica, and then by conversion to the hydrochloride salt using HCl in a solvent such as isopropanol as shown in Scheme 3 below.

Workup

  1. customby quenching with methanol

Sources & evidence

ORD record
ord-e314df6f58e9418280ca5406a7168fb6
Source dataset
uspto-grants-2016_06
Patent number
US09358237B2

Linked notes

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