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Ammonia → 4-(Bromoheptyl)-2,6-dimethyl pyridine

HRID 365699
Notes
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Reaction equation

HRID 365699 reaction equation
[N:1]1[C:6]([CH3:7])=[CH:5][C:4]([CH3:8])=[CH:3][C:2]=1[CH3:9].[Br:10][CH:11](Br)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].N>O1CCCC1>[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:8][C:4]1[CH:5]=[C:6]([CH3:7])[N:1]=[C:2]([CH3:9])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 222AmmoniaHCID 79532,4,6-TrimethylpyridineHCID 118068541,1-Dibromohexane

Product 1

HCID 178058604-(Bromoheptyl)-2,6-dimethyl pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

Sodium amide was formed from sodium (1.0 g, 43.5 mmol) in liquid ammonia (100 ml) according to Example 1. Collidine (1) (5.0 g, 41.3 mmol) dissolved in tetrahydrofuran (5 ml) was added dropwise and after 45 min a well-cooled solution of dibromohexane (51.2 g, 210 mmol) in THF (100 ml) was added quickly. The reaction mixture was stirred for 1 h at -40° C. and then left stirring overnight during which times ammonia evaporated.

Workup

  1. additionwas added quickly
  2. waitleft
  3. customevaporated

Sources & evidence

ORD record
ord-2f6847b9949c45f795afa97ecc22a46c
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06127529

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes