Hydrochloric Acid → HCID 11419393, compound

HRID 749663Notes

Reaction equation

HRID 749663 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:25]2([OH:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([NH:17]C(=O)OC(C)(C)C)[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[ClH:32]>C(OCC)C.O1CCOCC1>[ClH:1].[ClH:32].[NH2:17][CH:14]1[CH2:15][CH2:16][N:11]([CH2:10][CH:9]([C:25]2([OH:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86599032Tert-butyl{1-[2-(3,4-dichlorophenyl)-2-(1-hydroxycyclohexyl)ethyl]piperidin-4-yl}carbamate

Product 1

HCID 11419393HCID 11419393, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl {1-[2-(3,4-dichlorophenyl)-2-(1-hydroxycyclohexyl)ethyl]piperidin-4-yl}carbamate (130 mg, 0.28 mmol) (Example 13), in diethyl ether (2 mL) was treated with a 4 N solution of hydrogen chloride in dioxane (1 mL). The resulting solution was stored at 25° C. for 16 h, during which time crystals began to form. The mixture was transferred to the refrigerator where it was stored for an additional 16 h. The resulting crystals were collected, washed with diethyl ether, and dried in vacuo to yield 101 mg (82%) 1-[2-(4-aminopiperidin-1-yl)-1-(3,4-dichlorophenyl)ethyl]cyclohexanol dihydrochloride as a white solid. MS m/z 371/373/375 ([M+H]+); HRMS: calcd for C19H28Cl2N2O.2.00 HCl, 442.1112; found (ESI), 371.1642.

Workup

  1. customto form
  2. waitwas stored for an additional 16 h
  3. customThe resulting crystals were collected
  4. washwashed with diethyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c57ae835a4704c618ff8615a9e6ed0a0
Source dataset
uspto-grants-2008_07
Patent number
US07402698B2

Reaction notes

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