Water → HCID 18790020, compound

HRID 1462022Notes

Reaction equation

HRID 1462022 reaction equation
[C:1]12([NH2:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N(CC)CC)C.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:30][CH2:29][N:28]([CH:31]([CH3:34])[CH2:32]Br)[CH2:27][CH2:26]1.O>CN(C=O)C>[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:26][CH2:27][N:28]([CH:31]([CH3:34])[CH2:32][NH:11][C:1]23[CH2:8][CH:7]4[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]4)[CH2:2]2)[CH2:10]3)[CH2:29][CH2:30]1

Participants

6

Reactant 4

HCID 962WaterHCID 2130AmantadineHCID 8471TriethylamineHCID 13345142HCID 13345142, compound

Product 1

HCID 18790020HCID 18790020, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 1-adamantylamine (12.0 grams; 0.079 moles) in 250 cc of DMF is prepared. Triethylamine (21.9 cc; 0.158 moles), is added and the mixture is warmed to about 50° C. To the warm solution, there is added over a period of 3 hours, 1-(2-pyridyl)-4-(2-bromo-1-methylethyl)piperazine (18.0 grams; 0.063 moles) keeping the temperature about the same. The reaction mixture is poured into 500 cc of water and then extracted with ether. The ethereal phase, washed with water, then washed to neutrality and allowed to evaporate, gives as a residue, a crude oily product, which is purified by column chromatography. (THF-diisopropyl ether-Et3N 50:40:10). Compound (26) is an oil, which solidifies after prolonged standing; m.p. 67°-68° C. from n-hexane); Rf=0.22 (from ethyl acetate Et3N 9:1); IR (nujol) νmax: 1590, 1480, 1430, 1310, 1240, 1160, 775 cm-1 ; νN-H: 3250 cm-1 ; 1H-NMR (CDCl3): 0.93 (d, J=5 Hz; 3H); 1.20-2.23 (m; 16H); 2.23-3.00 (m; 7H); 3.20-3.70 (m; 4H); 6.40-6.73 (m; 2H; 7.23-7.63 (m; 1H); 8.03-8.27 (m; 1H); tripicrate: m.p. 185° C. (from ethanol).

Workup

  1. customis prepared
  2. additionTo the warm solution, there is added over a period of 3 hours
  3. extractionextracted with ether
  4. washThe ethereal phase, washed with water
  5. washwashed to neutrality
  6. customto evaporate
  7. customgives as a residue
  8. customa crude oily product, which is purified by column chromatography

Sources & evidence

ORD record
ord-843735da14a3416ebdf097773e7f65bc
Source dataset
uspto-grants-1984_07
Patent number
US04457931

Reaction notes

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