Hydrochloric Acid → HCID 69810935, compound

HRID 2190100Notes

Reaction equation

HRID 2190100 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[CH:22]([OH:24])[CH3:23])[N:15](C(OC(C)(C)C)=O)[CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:32]>C(Cl)Cl.O1CCOCC1>[ClH:32].[ClH:32].[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[CH:22]([OH:24])[CH3:23])[NH:15][CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69812790HCID 69812790, compound

Product 1

HCID 69810935HCID 69810935, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 1′-benzyl-4-(1-hydroxyethyl)spiro[indoline-3,4′-piperidine]-1-carboxylate (0.045 g, 0.11 mmol) in DCM (2 mL) was treated with 4N HCl in dioxane (0.5 mL). The reaction was stirred at room temperature for 4 hours and concentrated under reduced pressure to yield 1-(1′-benzylspiro[indoline-3,4′-piperidine]-4-yl)ethanol dihydrochloride (0.047 g, 100%), which was used without further purification. LCMS (APCI+) m/z 323.2 [M+H]+; Rt=2.38 min

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1436581c2e6f4d43b2585215791d62dd
Source dataset
uspto-grants-2012_12
Patent number
US08324221B2

Reaction notes

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