Water → HCID 17163945, compound

HRID 857911Notes

Reaction equation

HRID 857911 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[N+:9]([C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1)([O-:11])=[O:10].C(N(CC)CC)C.O>ClCCl>[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:16](=[O:17])[C:15]2[CH:14]=[CH:13][C:12]([N+:9]([O-:11])=[O:10])=[CH:20][CH:19]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 2283491-Methylhomopiperazine

Product 1

HCID 17163945HCID 17163945, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 1-methyl-[1,4]diazepane (2.19 mL) in dry dichloromethane (30 mL) was treated with a solution of 4-nitrobenzoyl chloride (3.6 g) in dry dichloromethane (30 mL) dropwise over 10 minutes. After stirring at room temperature for a further 10 minutes the reaction mixture was treated with triethylamine (2.8 mL) and then stirred for a further 3 hours. The reaction mixture was then treated with water (10 mL), the organic phase separated and further washed twice with a 2 M aqueous solution of sodium hydroxide (20 mL), then four times with water (15 mL). The organic phase was then dried over magnesium sulfate and evaporated to give the title compound (4.4 g) as brown oil, Rf 0.64 (dichloromethane:methanol, 4:1). MS: 264 [MH]+.

Workup

  1. stirringstirred for a further 3 hours
  2. customthe organic phase separated
  3. washfurther washed twice with a 2 M aqueous solution of sodium hydroxide (20 mL)
  4. dry with materialThe organic phase was then dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-2f45599235fd477fab438a7f280942b2
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

Loading…