Sodium Hydroxide → 3-(3-Aminopropyl)-1-phenyl-8-(1-phenylcycloheptyl)-1,3,8-triazaspiro[4.5]decan-4-one

HRID 991460Notes

Reaction equation

HRID 991460 reaction equation
[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][N:14]([C:17]4([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)[CH2:13][CH2:12]3)[C:10](=[O:30])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].C(OC([NH:40][CH2:41][CH2:42][CH2:43]Br)=O)(C)(C)C>C1(C)C=CC=CC=1.O.[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O>[NH2:40][CH2:41][CH2:42][CH2:43][N:9]1[C:10](=[O:30])[C:11]2([CH2:16][CH2:15][N:14]([C:17]3([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)[CH2:13][CH2:12]2)[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 98224551-Phenyl-8-(1-phenylcycloheptyl)-1,3,8-triazaspiro[4.5]decan-4-one

Product 1

HCID 98904673-(3-Aminopropyl)-1-phenyl-8-(1-phenylcycloheptyl)-1,3,8-triazaspiro[4.5]decan-4-oneYield 71.8%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Procedure

This was prepared according to the procedure of A. Petric et al. (Bioorg. Med. Chem. Lett. 1998, 8, 1455). To a stirred solution of 1-phenyl-8-(1-phenylcycloheptyl)-1,3,8-triazaspiro[4.5]decan-4-one (54.3 mg, 0.135 mmol) in toluene (0.3 ml) was added a solution of NaOH (23.8 mg, 0.595 mmol) in water (0.5 ml), n-Bu4NHSO4 (70.8 mg, 0.209 mmol), and a solution of N-(t-butoxycarbonyl)-3-bromopropylamine (65.3 mg, 0.274 mmol, this was reported by B. H. Lee et al. J. Org. Chem. 1983, 48, 24) in toluene (0.7 ml) at room temperature. The reaction mixture was stirred at room temperature for 18 h, then at 90° C. for 2 h. The reaction mixture was cooled down to room temperature, diluted with water, and extracted with CH2Cl2. The extracts combined were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by preparative TLC (1 mm plate×2, CH2Cl2/MeOH:95/5, two times developed) to afford 54.2 mg (71.8%) of colorless solid.

Workup

  1. customThis was prepared
  2. customat room temperature
  3. waitat 90° C. for 2 h
  4. temperatureThe reaction mixture was cooled down to room temperature
  5. extractionextracted with CH2Cl2
  6. washThe extracts combined were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by preparative TLC (1 mm plate×2, CH2Cl2/MeOH:95/5, two times developed)

Sources & evidence

ORD record
ord-bf9b664b41fa4cbea183b598c08eac1f
Source dataset
uspto-grants-2002_10
Patent number
US06465478B1

Reaction notes

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