Nalmefene → Nalmefene hydrochloride dihydrate

HRID 406935Notes

Reaction equation

HRID 406935 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-8f850933c9764d84a64375c65ddf3c23
Source dataset
uspto-grants-2014_06
Patent number
US08754217B2

Reaction notes

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