Hydrochloric Acid → 4-(2-Nitrophenoxy)piperidine--hydrogen chloride (1/1)

HRID 1093562Notes

Reaction equation

HRID 1093562 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:24].CCOCC>O1CCOCC1>[ClH:24].[N+:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[O:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 2794760Tert-butyl 4-(2-nitrophenoxy)piperidine-1-carboxylate

Product 1

HCID 467391574-(2-Nitrophenoxy)piperidine--hydrogen chloride (1/1)Yield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1H NMR (CDCl3): δ 7.8 (m, 1H), 7.6 (m, 1H), 7.0 (m, 2H), 4.7 (m, 1H), 3.6 (m, 4H), 1.9 (m, 4H), 1.5 (s, 9H). A solution of 4-(2-nitro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (1.5 g, 0.00465 mole) in dioxane.HCl (10 mL) was stirred at ambient temperature for 1 hour. Ether was then added the resulting precipitate was isolated by filtration and dried to afford 1 g (99%) of 4-(2-nitro-phenoxy)-piperidine hydrochloride. LCMS: 223.1 (M+1)+, 55%, 1H NMR (DMSO-d6): δ 9.0 (bs, 2H), 7.9 (m, 1H), 7.8 (m, 1H), 7.4 (m, 1H), 7.0 (m, 1H), 5.0 (m, 1H), 3.2 (m, 4H), 2.2 (m, 2H), 2.0 (m, 2H).

Workup

  1. customwas isolated by filtration
  2. customdried

Sources & evidence

ORD record
ord-78d8a70069b14528acf26182ccfb2e01
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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