Benzylamine → HCID 21833630, compound

HRID 1740841Notes

Reaction equation

HRID 1740841 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[CH2:18]([NH:25][C:2]1[N:7]=[C:6]([N:8]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 21833597HCID 21833597, compound

Product 1

HCID 21833630HCID 21833630, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 8 g 8-(2-chloro-pyrimidin-4-yl)-1,4-dioxa-8-aza-spiro[4.5]decane 8a) and 7.2 ml benzylamine is heated for 2 hours at 150° C., then cooled, admixed with 20 ml water and the aqueous solution is extracted three times with 20 ml methylene chloride each time. After drying the combined organic phases over sodium sulfate and removing the solvent, the residue is washed with cold isohexane. In this way 9.6 g benzyl-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-pyrimidin-2-yl]amine is obtained as a yellow powder. 1H-NMR (d6 -DMSO): δ=7.85 ppm (d, 1H); 7.40-7.18 (m, 5H) 7.15 (broad s, 1H, NH); 6.12 (d, 1H); 4.45 (d, 2H); 3.96 (s, 4H); 3.65 (m, 4H); 1.61 (m, 4H).

Workup

  1. temperaturecooled
  2. extractionthe aqueous solution is extracted three times with 20 ml methylene chloride each time
  3. dry with materialAfter drying the combined organic phases over sodium sulfate
  4. customremoving the solvent
  5. washthe residue is washed with cold isohexane

Sources & evidence

ORD record
ord-a39b2eb14da845cd9b143e7950ef6451
Source dataset
uspto-grants-1999_10
Patent number
US05972947

Reaction notes

Loading…