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Hydrochloric Acid → 4-[(4-Hydroxy-4-n-octyl)cyclohexylamino]-3-methoxy-2-methylpyridine

HRID 1009
Notes
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Reaction equation

HRID 1009 reaction equation
[Mg].[CH2:2](Br)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].O=[C:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[C:20]=2[O:26][CH3:27])[CH2:14][CH2:13]1.Cl.C1C[O:32]CC1>>[OH:32][C:5]([N:18]([CH:15]1[CH2:16][CH2:17][CH2:12][CH2:13][CH2:14]1)[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[C:20]=1[O:26][CH3:27])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][CH2:3][CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 81401-BromooctaneHCID 5462224MagnesiumHCID 196939514-(4-Oxocyclohexylamino)-3-methoxy-2-methylpyridine

Product 1

HCID 677539694-[(4-Hydroxy-4-n-octyl)cyclohexylamino]-3-methoxy-2-methylpyridine

Procedure

The Grignard solution is prepared from 0.73 g of magnesium and 6.0 g of octyl bromide in 50 ml of absolute THF. 2.8 g of 4-(4-oxocyclohexylamino)-3-methoxy-2-methylpyridine in 20 ml of THF are added dropwise to the solution. After 2 hours the mixture is acidified with 2N HCl. The THF is then distilled off in vacuo at room temperature and the product is extracted from the solution which is rendered alkaline with methylene chloride. Further working up takes place as in the previous working procedure.

Workup

  1. distillationThe THF is then distilled off in vacuo at room temperature
  2. extractionthe product is extracted from the solution which

Sources & evidence

ORD record
ord-8babbf86aa35457596df795b424dbf27
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723450

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes