Nalmefene → Nalmefene hydrochloride dihydrate

HRID 40873Notes

Reaction equation

HRID 40873 reaction equation
[CH2:1]=[C:2]1[C@@H:15]2[O:16][C:12]3[C:13]4[C@:14]52[CH2:17][CH2:18][N:19]([CH2:20][CH:21]2[CH2:23][CH2:22]2)[C@H:6]([CH2:7][C:8]=4[CH:9]=[CH:10][C:11]=3[OH:24])[C@:5]5([OH:25])[CH2:4][CH2:3]1.[ClH:26].C=C1[C@@H]2[O:42]C3C4[C@]52CCN(CC2CC2)[C@H](CC=4C=CC=3O)[C@]5(O)CC1>>[CH2:1]=[C:2]1[C@@H:15]2[O:16][C:12]3=[C:11]([OH:24])[CH:10]=[CH:9][C:8]4=[C:13]3[C@:14]32[CH2:17][CH2:18][N:19]([CH2:20][CH:21]2[CH2:22][CH2:23]2)[C@H:6]([CH2:7]4)[C@:5]3([OH:25])[CH2:4][CH2:3]1.[OH2:42].[OH2:16].[ClH:26]

Participants

3

Reactant 2

HCID 5284594NalmefeneHCID 5388881Nalmefene hydrochloride

Product 1

HCID 46209574Nalmefene hydrochloride dihydrate

Conditions

Temperature
20 °C

Procedure

At 50° C., Nalmefene Hydrochloride was added as seeding. The seed did not dissolve and Nalmefene started to crystallize. When the cooling ramp was terminated the suspension was maintained under stirring at 20° C. for 2.5 days. The solid was filtered and washed with acetone (50 ml). The wet product was dried overnight under vacuum at 40° C. yielding 13.2 g of Nalmefene hydrochloride dihydrate (chemical purity 99.74%, water content 8.54% w/w as measured by Karl Fisher titration).

Workup

  1. dissolutionThe seed did not dissolve
  2. customto crystallize
  3. customWhen the cooling ramp was terminated the suspension
  4. temperaturewas maintained
  5. filtrationThe solid was filtered
  6. washwashed with acetone (50 ml)
  7. customThe wet product was dried overnight under vacuum at 40° C.

Sources & evidence

ORD record
ord-cc909c6d7bfc4c6f9c479997830e2d7f
Source dataset
uspto-grants-2013_09
Patent number
US08530495B2

Reaction notes

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