Hydrochloric Acid → Almorexant hydrochloride

HRID 1879324Notes

Reaction equation

HRID 1879324 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C@H:9]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)[N:8]([C@H:27]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:28]([NH:30][CH3:31])=[O:29])[CH2:7][CH2:6]2.[ClH:38]>>[ClH:38].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C@H:9]([CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]([F:25])([F:24])[F:26])=[CH:21][CH:22]=1)[N:8]([C@H:27]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:28]([NH:30][CH3:31])=[O:29])[CH2:7][CH2:6]2

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 23727689Almorexant

Product 1

HCID 25227440Almorexant hydrochloride

Procedure

To the organic phase of step 11 is added 1 equivalent aqueous hydrochloric acid and then the water removed by azeotropic distillation in vacuo. The precipitate is dissolved by addition of 2-propanol at 75° C. Concentration of the solution leads to crystallisation and the suspension is then cooled to RT. To ensure complete crystallisation, the suspension is aged at RT, then filtered and washed with a MIBK-2-propanol mixture. The product is dried in vacuo at 50° C.

Workup

  1. customthe water removed by azeotropic distillation in vacuo
  2. dissolutionThe precipitate is dissolved by addition of 2-propanol at 75° C
  3. customConcentration of the solution leads to crystallisation
  4. customcrystallisation
  5. customis aged at RT
  6. filtrationfiltered
  7. washwashed with a MIBK-2-propanol mixture
  8. customThe product is dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-64e232f89bf64011a844610f53e2f3fc
Source dataset
uspto-grants-2012_11
Patent number
US08314238B2

Reaction notes

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