Dichloromethane → HCID 11695946, compound

HRID 1639968Notes

Reaction equation

HRID 1639968 reaction equation
Cl.[CH:2]1([N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)[C:9]2=[O:18])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(Cl)Cl.[CH:22](N(CC)C(C)C)(C)[CH3:23].C1N=CN([C:36]([N:38]2[CH:42]=N[CH:40]=[CH:39]2)=[O:37])C=1.N1CCCCC1>>[CH:2]1([N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][CH2:15][N:14]([C:36]([N:38]4[CH2:39][CH2:40][CH2:23][CH2:22][CH2:42]4)=[O:37])[CH2:13]3)[C:9]2=[O:18])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8082PiperidineHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 66722385HCID 66722385, compound

Product 1

HCID 11695946HCID 11695946, compound

Procedure

To a solution of 2-cyclohexyl-2,7-diazaspiro[4.5]decan-1-one hydrochloride (20 mg, 0.00007 mol) in methylene chloride (0.5 mL, 0.008 mol) was added N,N-diisopropylethylamine (14.0 μL, 0.0000806 mol) and the solution was stirred at rt for 5 min. prior to the addition of N,N-carbonyldiimidazole (24 mg, 0.00015 mol). After stirring the reaction mixture at rt for 3 h, piperidine (6.2 mg, 0.00007 mol) was added and stirring was continued for 12 h. To drive the reaction to completion the mixture was heated at 170° C. under microwave irradiation for 1 h. The crude mixture was purified by prep.-HPLC to afford the desired product. LC-MS: 348.2 (M+H)+.

Workup

  1. stirringAfter stirring the reaction mixture at rt for 3 h
  2. stirringstirring
  3. waitwas continued for 12 h
  4. customthe reaction to completion the mixture
  5. temperaturewas heated at 170° C. under microwave irradiation for 1 h
  6. customThe crude mixture was purified by prep.-HPLC

Sources & evidence

ORD record
ord-1f7696ec2c6545a983d6621ec32989e6
Source dataset
uspto-grants-2012_02
Patent number
US08110581B2

Reaction notes

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