Acetyl chloride → HCID 22141181, compound

HRID 428928Notes

Reaction equation

HRID 428928 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=2)[CH3:13])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29].[Cl-].[NH4+]>ClCCl>[NH3:7].[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:15]=[C:16]([NH:20][C:28](=[O:30])[CH3:29])[CH:17]=[CH:18][CH:19]=2)[CH3:13])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 221413223-(3-Hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine

Product 2

HCID 222AmmoniaHCID 22141181HCID 22141181, compoundYield 198.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3-hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine (Preparation 12, 1.30 g, 4.8 mmol) and triethylamine (3.34 ml, 24.0 rnuol) in dichloromethane (30 ml) at room temperature was slowly added acetyl chloride (0.48 ml, 6.72 mmol). The mixture was stirred at room temperature overnight and then saturated ammonium chloride solution (50 ml) was added. The two layers were separated and the aqueous layer was extracted with dichloromethane (3×20 ml). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica column chromatography eluting with ethyl acetate:methanol:ammonia solution (0.880) (90:10:1) to afford the title compound (1.5 g, 100%) as a colourless gum.

Workup

  1. customat room temperature
  2. customThe two layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (3×20 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by silica column chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-3d954985c77848baa75b888e62130ef2
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

Loading…