1-(3-Chloropropyl)-4-phenylpiperidine → 7-methoxy-4-(1-methylethyl)-6-[3-(4-phenyl-1-piperidinyl)propoxy]-2H-1-benzopyran-2-one

HRID 22332

Reaction equation

HRID 22332 reaction equation
[OH:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][C:5]2[O:10][C:9](=[O:11])[CH:8]=[C:7]([CH:12]([CH3:14])[CH3:13])[C:6]=2[CH:15]=1.Cl[CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:24][CH2:23]1.C([O-])(=O)/C=C/C([O-])=O>CC(OC)(C)C.CC(C)=O>[CH3:17][O:16][C:3]1[C:2]([O:1][CH2:19][CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:26][CH2:27]2)=[CH:15][C:6]2[C:7]([CH:12]([CH3:13])[CH3:14])=[CH:8][C:9](=[O:11])[O:10][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 2036891-(3-Chloropropyl)-4-phenylpiperidineHCID 5460307FumarateHCID 19927654HCID 19927654, compound

Product 1

HCID 199276387-methoxy-4-(1-methylethyl)-6-[3-(4-phenyl-1-piperidinyl)propoxy]-2H-1-benzopyran-2-oneYield 85%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 15413tert-Butyl methyl etherSolvent2×

Procedure

Method D (2.5 h at 85° C.); starting materials: 6-hydroxy-7-methoxy-4-(1-methylethyl)-2H-1-benzopyran-2-one (example 105) and 1-(3-chloropropyl)-4-phenyl-piperidine; yield 85%; fusion point 62°-65° C. (from TBME). Fumarate: method E; yield 65%; fusion point 155°-157° C. (from acetone, boiled out with TBME).

Workup

  1. customMethod D (2.5 h at 85° C.)
  2. customfusion point 155°-157° C.

Sources & evidence

ORD record
ord-13dfe9d867b84ecfb63a521715149af8
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Linked notes

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