Hydrochloric Acid → HCID 86642703, compound

HRID 2061074Notes

Reaction equation

HRID 2061074 reaction equation
[N:1]([C:4]([CH3:10])([CH3:9])[CH2:5][C:6](Cl)=[O:7])=[N+:2]=[N-:3].[NH:11]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.Cl>ClCCCl>[N:11]1([C:6](=[O:7])[CH2:5][C:4]([N:1]=[N+:2]=[N-:3])([CH3:10])[CH3:9])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8119AzepaneHCID 601345073-Azido-3-methylbutanoyl chloride

Product 1

HCID 86642703HCID 86642703, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred ice cold solution of 3-azido-3-methylbutanoyl chloride (8.00 g, 49.5 mmol) in anhydrous DCE (160 mL) was added azepane (12.6 mL, 3 equiv, 0.11 mol) in one portion. The reaction was stirred and left at 0° C. for 15 min and room temperature for 45 min. Aqueous 1 M HCl (100 mL) was added to the reaction mixture and the contents poured into a separatory funnel. The organic layer was separated and washed with 1 M HCl (100 mL) and saturated NaHCO3 (150 mL). It was dried over anhydrous MgSO4, filtered, concentrated and dried under high vacuum to give a crude oil (8.24 g, quant). This material was used without further purification. LRMS (ESI+) for C11H20N4O (224.1); Found: 225 (MH+).

Workup

  1. additionthe contents poured into a separatory funnel
  2. customThe organic layer was separated
  3. washwashed with 1 M HCl (100 mL) and saturated NaHCO3 (150 mL)
  4. dry with materialIt was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried under high vacuum
  8. customto give a crude oil (8.24 g, quant)
  9. customThis material was used without further purification

Sources & evidence

ORD record
ord-9846e14ca32b436d87c7fd6fdd5f78d0
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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