4-Methoxybutanoyl chloride → tert-Butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[2-(4-methoxybutyrylamino)-4-methylbenzyloxy]piperidine-1-carboxylate

HRID 1176387Notes

Reaction equation

HRID 1176387 reaction equation
[NH2:1][C:2]1[CH:42]=[C:41]([CH3:43])[CH:40]=[CH:39][C:3]=1[CH2:4][O:5][CH:6]1[CH:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])=[CH:14][CH:13]=2)[CH2:10][CH2:9][N:8]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:7]1.[CH3:44][O:45][CH2:46][CH2:47][CH2:48][C:49](Cl)=[O:50]>N1C=CC=CC=1.ClCCl>[CH3:31][O:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][O:22][CH2:21][CH2:20][CH2:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH:11]2[CH2:10][CH2:9][N:8]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:7][CH:6]2[O:5][CH2:4][C:3]2[CH:39]=[CH:40][C:41]([CH3:43])=[CH:42][C:2]=2[NH:1][C:49](=[O:50])[CH2:48][CH2:47][CH2:46][O:45][CH3:44])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 127949894-Methoxybutanoyl chlorideHCID 68504488Tert-butyl 3-(2-amino-4-methylbenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Product 1

HCID 68571336tert-Butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[2-(4-methoxybutyrylamino)-4-methylbenzyloxy]piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

The solution of 0.278 g of tert-butyl 3-(2-amino-4-methylbenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 0.046 ml of pyridine and 2.3 ml of dichloromethane is cooled to 0° C. and admixed slowly with 0.078 g of 4-methoxybutyryl chloride. The reaction mixture is concentrated by evaporation. The title compound is obtained as a yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.06 (1:1 EtOAc-heptane); Rt=5.86.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation

Sources & evidence

ORD record
ord-2e099fd53a094127b8628c1dd2ea1071
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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