Acetamide → 4-Piperidinopiperidine-1-carbonyl chloride

HRID 1037627

Reaction equation

HRID 1037627 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.C(N)(=[O:35])C.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 178AcetamideHCID 1049PyridineHCID 6344Dichloromethane2×HCID 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 (20 g), methylene dichloride, acetamide (3 gm) and pyridine (60 ml) under nitrogen atmosphere. A solution of [1,4′]bipiperidinyl-1′-carbonyl chloride (17.6 g), methylene dichloride and triethylamine (20 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. The crystalline compound was filtered, washed with hexane and dried under reduced pressure at 50° C. The yield was 28.4 g (95%). 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
  6. filtrationThe crystalline compound was filtered
  7. washwashed with hexane
  8. customdried under reduced pressure at 50° C

Sources & evidence

ORD record
ord-6518246a8d4847cfa3c153f2d56092e4
Source dataset
uspto-grants-2013_10
Patent number
US08546573B2

Linked notes

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