Hydrochloric Acid → HCID 19591383, compound

HRID 1957054Notes

Reaction equation

HRID 1957054 reaction equation
C1(C)C=C[C:4]([S:7]([OH:10])(=[O:9])=[O:8])=CC=1.[C:12]([C:15]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)(O)=O.B.CO.Cl>C1COCC1.CCOCC>[CH3:4][S:7]([OH:10])(=[O:9])=[O:8].[C:21]1([C:15]23[CH2:12][N:18]([CH2:19][CH2:20]2)[CH2:17][CH2:16]3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6331BoraneHCID 27236574-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 19591383HCID 19591383, compoundYield 151.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10.25 g of 4-carboxy-4-phenyl piperidine p-toluenesulfonate and 150 ml of a 1M solution of borane in THF is refluxed for 1 hour. 30 ml of MeOH are added under the action of heat and over 20 minutes, then after cooling to RT, a saturated solution of gaseous HCl in ether is added until the pH is 1 and the reaction mixture is left under stirring overnight at RT. The solvents are concentrated under vacuum, the residue is taken up with acetone and then with ether to give 11,1 g of the expected product, M.p.=263° C.

Workup

  1. temperatureis refluxed for 1 hour
  2. temperatureof heat and over 20 minutes
  3. waitthe reaction mixture is left
  4. concentrationThe solvents are concentrated under vacuum

Sources & evidence

ORD record
ord-d803d2bfb418497298bd70bbe5d5570c
Source dataset
uspto-grants-1998_07
Patent number
US05780466

Reaction notes

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