Pyridine → 4-Piperidinopiperidine-1-carbonyl chloride

HRID 1037629

Reaction equation

HRID 1037629 reaction equation
CCC1C=CC(=O)[C:5]2=C[C:7]3[CH2:25][N:24]4[C:10](=[CH:11][C:12]5[C@@](O)(CC)C(=O)OC[C:13]=5[C:22]4=O)[C:8]=3[NH:9][C:4]=12.[CH2:30]([Cl:32])Cl.CC(N(C)C)=[O:35].N1C=CC=CC=1>C(N(CC)CC)C>[N:24]1([CH:25]2[CH2:5][CH2:4][N:9]([C:30]([Cl:32])=[O:35])[CH2:8][CH2:7]2)[CH2:22][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344Dichloromethane2×HCID 31374DimethylacetamideHCID 178436639(19S)-5,19-diethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),4,6,9,15(20)-hexaene-8,14,18-trione

Product 1

HCID 98133754-Piperidinopiperidine-1-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
35 °C

Procedure

In a suitable vessel were charged 7-Ethyl-10-hydroxycamptothecin (1 g), methylene dichloride, dimethyl acetamide (0.221 gm) and pyridine (3 ml) under nitrogen atmosphere. A solution of [1,4′]bipiperidinyl-1′-carbonyl chloride (0.88 g), methylene dichloride and triethylamine (1 ml) was prepared and added to the above suspension and stirred at 30-40° C. for 2 hours. The solvent was distilled out under reduced pressure at 50° C. and hexane was added under stirring as an antisolvent to isolate crystalline compound which was then filtered, washed with hexane and dried under reduced pressure at 50° C. The yield was 1.25 g (83.55%); HPLC purity-99.9%

Workup

  1. additionadded to the above suspension
  2. distillationThe solvent was distilled out under reduced pressure at 50° C.
  3. additionhexane was added
  4. stirringunder stirring as an antisolvent
  5. customto isolate crystalline compound which
  6. filtrationwas then filtered
  7. washwashed with hexane
  8. customdried under reduced pressure at 50° C

Sources & evidence

ORD record
ord-938865b02c574c959ca0ee610d8a1e98
Source dataset
uspto-grants-2013_10
Patent number
US08546573B2

Linked notes

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