Hydrochloric Acid → 8,10-Difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol hydrochloride salt

HRID 1513930Notes

Reaction equation

HRID 1513930 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:17](=[C:18]([F:20])[CH:19]=1)[C:16]1[C:7](=[C:8]3[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([OH:21])[CH:10]=[CH:9]3)[CH:6]([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)[O:5]2.[ClH:37]>ClCCl>[ClH:37].[F:1][C:2]1[CH:3]=[C:4]2[C:17](=[C:18]([F:20])[CH:19]=1)[C:16]1[C:7](=[C:8]3[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([OH:21])[CH:10]=[CH:9]3)[CH:6]([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)[O:5]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 111676898,10-Difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol

Product 1

HCID 670047448,10-Difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol hydrochloride saltYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 8,10-difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol (532 mg, 1.1 mmol) in dichloromethane (10 mL) and add 2M HCl (1.1 mL, 2.2 mmol) and stir for 10 minutes. Concentrate in vacuo to yield 536 mg (100%) of the title compound. Mass spectrum (ion spray): m/z=488 (M+H−HCl). Separate the racemate into its constituent enantiomers by chiral chromatography. Conditions: Column: Chiralcel OD 4.6×150 mm; Eluent: 0.2% DMEA, 5% MeOH, 10% 3A Alcohol in Heptane.

Workup

  1. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-9dee3cbd8bdc4de3b7c534d36eb79cd3
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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