Oxalic Acid → HCID 67753679, compound

HRID 258286Notes

Reaction equation

HRID 258286 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C@H:12]3[CH2:16][C@:5]([CH2:17][N:18]4[CH2:23][CH2:22][CH:21]([NH:24][C:25](=[O:30])[CH2:26][O:27][CH2:28][CH3:29])[CH2:20][CH2:19]4)([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1.[C:31]([OH:36])(=[O:35])[C:32]([OH:34])=[O:33]>CCOCC>[C:31]([OH:36])(=[O:35])[C:32]([OH:34])=[O:33].[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C@H:12]3[CH2:16][C@:5]([CH2:17][N:18]4[CH2:19][CH2:20][CH:21]([NH:24][C:25](=[O:30])[CH2:26][O:27][CH2:28][CH3:29])[CH2:22][CH2:23]4)([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 9932172HCID 9932172, compound

Product 1

HCID 67753679HCID 67753679, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of N-(1-[(9S,10S)-(+)-2-chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)-2-ethoxyacetamide (2.24 g, 5.27 mmol) in ether (50 mL) was added a solution of oxalic acid (0.47 g, 5.27 mmol) in ether (5 mL). The resulting solid was filtered and dried (0.05 mm/80 C) to give the title compound as a white solid (2.26 g, 83%), mp 193.0°-3.5° C.; MS(CI): 425 (M+H); NMR (300 MHz,DMSO-d6): 1.14(t, 3H, J=7.0 Hz), 1.67-1.79(br m, 4H), 2.58(s, 2H), 2.79(m, 2H), 3.25(m, 2H), 3.47(q, 2H, J=7.0 Hz), 3.70-3.88(br m, 3H), 4.41(s, 1H), 6.98(m, 3H), 7.30(m, 4H), 7.68(m, 1H).

Workup

  1. filtrationThe resulting solid was filtered
  2. customdried (0.05 mm/80 C)

Sources & evidence

ORD record
ord-0f2d628fd7ee4750bd871040d1599a4a
Source dataset
uspto-grants-1993_11
Patent number
US05266570

Reaction notes

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