Hydrochloric Acid → 7,9-Difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol hydrochloride salt

HRID 1513923Notes

Reaction equation

HRID 1513923 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]2[C:3]=1[O:4][CH:5]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:24][CH:23]=1)[C:6]1[C:15]2=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([OH:21])=[CH:11]2.[ClH:37].CCOCC>C(Cl)Cl>[ClH:37].[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]2[C:3]=1[O:4][CH:5]([C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)=[CH:26][CH:27]=1)[C:6]1[C:15]2=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([OH:21])=[CH:11]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 117850637,9-Difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol

Product 1

HCID 670045857,9-Difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol hydrochloride saltYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 7,9-difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol (1.6 g, 3.3 mmol) in methylene chloride (20 mL). Add 2M HCl in ether (3.3 mL, 6.6 mmol) and concentrate in vacuo. Dissolve the residue in methylene chloride (5 mL) and add dropwise to vigorously stirred ether (30 mL). Filter the precipitate and dry in a 50° C. vacuum oven overnight to obtain 1.5 g (87%) of the title compound. Mass spectrum (ion spray): m/z=488.3 (M+H−HCl).

Workup

  1. concentrationconcentrate in vacuo
  2. dissolutionDissolve the residue in methylene chloride (5 mL)
  3. additionadd dropwise to vigorously stirred ether (30 mL)
  4. filtrationFilter the precipitate
  5. customdry in a 50° C. vacuum oven overnight

Sources & evidence

ORD record
ord-db292954e3604b609c6075153bf71c04
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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