Hydrochloric Acid → 1-(3-(12H-Dibenzo[d,g][1,3]dioxocin-12-ylidene)-1-propyl)-4-piperidinecaboxylic acid hydrochloride

HRID 1417033Notes

Reaction equation

HRID 1417033 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH:14]=[C:15]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[O:20][CH2:19][O:18][C:17]3[CH:27]=[CH:28][CH:29]=[CH:30][C:16]2=3)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].[ClH:33]>C(O)C.ClCCl>[ClH:33].[CH:30]1[C:16]2[C:15](=[CH:14][CH2:13][CH2:12][N:9]3[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[O:20][CH2:19][O:18][C:17]=2[CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 508523541-(3-(12H-dibenzo[d,g][1,3]dioxocin-12-ylidene)-1-propyl)-4-piperidinecarboxylic acid ethyl ester

Product 1

HCID 701015381-(3-(12H-Dibenzo[d,g][1,3]dioxocin-12-ylidene)-1-propyl)-4-piperidinecaboxylic acid hydrochlorideYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

The above ester (2.30 g, 5.6 mmol) was dissolved in ethanol (30 ml), a 20% solution of sodium hydroxide (3.5 ml) was added and the mixture was stirred at room temperature for 7 h. The solution was diluted with dichloromethane (240 ml) and acidified with concentrated hydrochloric acid (3 ml). The mixture was washed with water (10 ml), the organic phase was dried over MgSO4 and evaporated in vacuo. The solid residue was washed with acetone, filtered off and dried in vacuo, affording the title compound (1.8 g, 73%).

Workup

  1. washThe mixture was washed with water (10 ml)
  2. dry with materialthe organic phase was dried over MgSO4
  3. customevaporated in vacuo
  4. washThe solid residue was washed with acetone
  5. filtrationfiltered off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-3ad272524e954e479c39cc039ec08fc3
Source dataset
uspto-grants-1999_06
Patent number
US05917047

Reaction notes

Loading…