Formamide → HCID 18414049, compound

HRID 991457Notes

Reaction equation

HRID 991457 reaction equation
S(=O)(=O)(O)O.C(N)=O.[C:9]1([N:15]2[C:19]3([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:18](=[O:25])[NH:17][CH2:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O>[C:9]1([N:15]2[C:19]3([CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)[C:18](=[O:25])[N:17]=[CH:16]2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 713Formamide2×HCID 1118Sulfuric AcidHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-one

Product 1

HCID 18414049HCID 18414049, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

As shown in Scheme 2, Compounds (I) wherein R is hydrogen can be prepared from a piperidine-4-one (V) through a compound (VI) according to known procedures as described in U.S. Pat. No. 3,238,216. First, the compound (V) can be reacted with a hydrochloric acid salt of an amino compound (VII) (i.e., XNH2) in the presence of a suitable cyanating agent such as potassium cyanide (KCN), to give the compound (VI). This reaction can be carried out in a suitable reaction inert solvent such as water at 0° to 50° C. for 30 min. to 7 days. Then, the compound (VI) may be treated with sulfuric acid at 0° to 100° C. for 30 min. to 10 hours, followed by reaction with formamide (HCONH2). The reaction with formamide may be carried out at 150° to 250° C. for 30 min. to 20 hours. If a mixture of 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one derivative and 1-phenyl-1,3,8-triazaspiro[4.5]dec-2-en-4-one derivative is obtained in this reaction condition, the mixture may be treated with a reducing reagent such as sodium borohydride (NaBH4) to give desired 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one derivative.

Workup

  1. customThis reaction
  2. waitmay be carried out at 150° to 250° C. for 30 min. to 20 hours

Sources & evidence

ORD record
ord-54e2c0de36f34f22802fc2a612607660
Source dataset
uspto-grants-2002_10
Patent number
US06465478B1

Reaction notes

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