Hydrochloric Acid → HCID 18474273, compound

HRID 651528Notes

Reaction equation

HRID 651528 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)[CH:7]=1.Cl>C(Cl)Cl.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18474280HCID 18474280, compound

Product 1

HCID 18474273HCID 18474273, compoundYield 199.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 215 mg of 1-[(2-chlorophenoxy)methyl]-3-[[N-(tert-butoxycarbonyl)piperidin-4-yl]methoxy]benzene, as prepared in the preceding step, in methylene chloride (2 mL) was treated with 1.5 mL of 4 N HCl in dioxane. The reaction mixture was stirred at ambient temperature for 1 h, and then concentrated to provide 183 mg of the title compound as a colorless powder after repeated concentrations from diethyl ether/hexane/methanol. 1H-NMR (300 MHz, DMSO-d6) δ 8.51 (br s, 2 H), 7.45 (dd, 1 H, J=1.3, 7.9 Hz), 7.27-7.35 (m, 2 H), 7.21 (d, 1 H), 6.90-7.05 (m, 4 H), 5.18 (s, 2 H), 3.87 (d, 2 H), 2.90 (t, 2 H, J=10 Hz), 2.05 (m, 1 H), 1.91 (d, 2 H, J=13.8 Hz), and 1.5-1.54 (m, 2 H). Mass spectrum (MALDI-TOF; α-cyano-4-hydroxycinnamic acid matrix) calcd. for C19H22ClNO2: 332.1 (M+H). Found: 332.0.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-856ea3d818264570a2a88886e9761a12
Source dataset
uspto-grants-2001_08
Patent number
US06281206B1

Reaction notes

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