Hydrochloric Acid → 3-{4-[4-((r)-1-Pyrrolidin-2-ylmethoxy)-phenoxy]-phenyl}-pyridine hydrochloride salt

HRID 1909714Notes

Reaction equation

HRID 1909714 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.[ClH:34]>O1CCOCC1>[ClH:34].[NH:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[CH:24][CH:23]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69003810(R)-2-[4-(4-Pyridin-3-yl-phenoxy)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 690001893-{4-[4-((r)-1-Pyrrolidin-2-ylmethoxy)-phenoxy]-phenyl}-pyridine hydrochloride saltYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of the product from step 3 (100 mg, 0.22 mmol) in dioxane (1 mL) was added 4M HCl in dioxane (5 mL) at rt and the resulting mixture was stirred for 2 h at that temperature. Solvent was removed in vacuo, residue was triturated with ether and dried under vacuum to obtain the title product (79 mg, 95%): MS; m/z 347.7 (M+H); 1H NMR (400 MHz, DMSO-d6); δ 1.72-1.77 (m, 1H), 1.90-2.00 (m, 2H), 2.11-2.15 (m, 1H), 3.21-3.24 (m, 2H), 3.89-3.91 (m, 1H), 4.15-4.19 (m, 2H), 7.05-7.13 (m, 6H), 7.83-7.86 (m, 2H), 7.94 (dd, 2H, J1=5.2 Hz, J2=8 Hz), 8.63 (d, 1H, J=7.6 Hz), 8.77 (dd, 1H, J1=5.2 Hz, J2=1.2 Hz), 9.13 (d, 2H, J=2 Hz), 9.67 (br, 3H); HPLC (UV); 97%.

Workup

  1. customSolvent was removed in vacuo, residue
  2. customwas triturated with ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-f19a99053ca84814a2e40146d7e8e741
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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