Hydrochloric Acid → HCID 68518873, compound

HRID 732745Notes

Reaction equation

HRID 732745 reaction equation
[ClH:1].[CH2:2]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23]C)[CH:19]=3)[C:14]=2[O:25][C:26]2[CH:40]=[CH:39][C:29]([O:30][CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:28][CH:27]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:3].C(S(C1C=CC(C2C(OC3C=CC(OCCN4CCCCC4)=CC=3)=C3C(=CC=2)C=C(O)C=C3)=CC=1)(=O)=O)C.Cl>C(OCC)(=O)C.C(OCC)C>[ClH:1].[CH2:2]([S:4]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:14]([O:25][C:26]3[CH:40]=[CH:39][C:29]([O:30][CH2:31][CH2:32][N:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)=[CH:28][CH:27]=3)=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[C:18]([OH:23])[CH:17]=[CH:16]3)=[CH:11][CH:12]=1)(=[O:5])=[O:6])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10324755HCID 10324755, compoundHCID 68518332HCID 68518332, compound

Product 1

HCID 68518873HCID 68518873, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Using the product from Example 13 (1.5 g, 2.58 mmol) and the procedure described in Example 3, prepare 1.35 grams of 6-(4-ethanesulfonyl-phenyl)-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-ol. Dissolve the free base in a mixture of ethyl acetate and diethyl ether (60 mL; 1:1). Cool in an ice bath and treat with 2M HCl in diethyl ether (2 mL, 4 mmol). Collect the precipitate on filter paper, rinse with diethyl ether and dry at 50° C. (<2 mm of Hg) for 18 hours to give 1.3 grams of the title compound (89%): mass spectrum (ion spray): m/z=532.3 (M+H).

Workup

  1. dissolutionDissolve the free base
  2. temperatureCool in an ice bath
  3. customCollect the precipitate
  4. filtrationon filter paper
  5. washrinse with diethyl ether
  6. customdry at 50° C. (<2 mm of Hg) for 18 hours

Sources & evidence

ORD record
ord-bb2c99dc6b3846819a96f72a5e543088
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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