Pyrrolidine → HCID 86749447, compound

HRID 1721289Notes

Reaction equation

HRID 1721289 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[N:3]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>>[Cl:1][C:2]1[N:7]=[C:6]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:5]=[C:4]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[N:3]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 86749448HCID 86749448, compound

Product 1

HCID 86749447HCID 86749447, compound

Procedure

After adding 2.00 g (3.81 mmoles) of 1- (3α,16α)-eburnamenine-14-carbonyl!-4-(2,4-dichloro-6-pyrimidinyl)piperazine in small portions to 20 ml of pyrrolidine at a temperature below 10° C., the reaction mixture is stirred at room temperature for 1 hour, then evaporated. After distributing the evaporation residue between 40 ml of chloroform and 10 ml of 1% sodium hydroxide solution the organic phase is separated, dried and evaporated. The evaporation residue is subjected to chromatography on a silica gel column. By using a 99:1 mixture of chloroform and methanol the less polar 1- (3α,16α)-eburnamenine-14-carbonyl!-4-(4-chloro-2-pyrrolidino-6-pyrimidinyl)piperazine is first eluted from the column, which is recrystallized from a mixture of ether and hexane to give a yield of 2.01 g (88.2%), m.p.: 210°-220° C. By further elution the more polar 1- (3α,16α)-eburnamenine-14-carbonyl!-4-(2-chloro-4-pyrrolidino-6-pyrimidinyl)piperazine is obtained which is similarly recrystallized from a mixture of ether and hexane to give a yield of 0.13 g (5.7%), m.p.: 169°-200° C.

Workup

  1. additionAfter adding 2.00 g (3.81 mmoles) of 1- (3α,16α)-eburnamenine-14-carbonyl
  2. customevaporated
  3. customis separated
  4. customdried
  5. customevaporated
  6. additiona 99:1 mixture of chloroform and methanol the less polar 1- (3α,16α)-eburnamenine-14-carbonyl
  7. wash-4-(4-chloro-2-pyrrolidino-6-pyrimidinyl)piperazine is first eluted from the column, which
  8. customis recrystallized from a mixture of ether and hexane
  9. customto give a yield of 2.01 g (88.2%), m.p.: 210°-220° C
  10. washBy further elution the more polar 1- (3α,16α)-eburnamenine-14-carbonyl

Sources & evidence

ORD record
ord-3a6296eadc2249acbd9ae45910d8471f
Source dataset
uspto-grants-1996_04
Patent number
US05510345

Reaction notes

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