Tributyltin azide → HCID 178489540, compound

HRID 1176390Notes

Reaction equation

HRID 1176390 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][C:6]1[CH:48]=[CH:47][CH:46]=[CH:45][C:7]=1[O:8][CH2:9][CH2:10][O:11][CH:12]1[CH:17]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])=[CH:20][CH:19]=2)[CH2:16][CH2:15][N:14]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:13]1)#[N:2].C([Sn]([N:62]=[N+:63]=[N-:64])(CCCC)CCCC)CCC>CC1C=CC=CC=1C>[CH3:37][O:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH2:29][O:28][CH2:27][CH2:26][CH2:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH:17]2[CH2:16][CH2:15][N:14]([C:38]([O:40][C:41]([CH3:44])([CH3:42])[CH3:43])=[O:39])[CH2:13][CH:12]2[O:11][CH2:10][CH2:9][O:8][C:7]2[CH:45]=[CH:46][CH:47]=[CH:48][C:6]=2[CH2:5][CH2:4][CH2:3][C:1]2[NH:64][N:63]=[N:62][N:2]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 68499085HCID 68499085, compound

Product 1

HCID 178489540HCID 178489540, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 0.40 g of tert-butyl 3-{2-[2-(3-cyanopropyl)phenoxy]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate (Example 55a) and 0.34 ml of tributyltin azide in 8 ml of o-xylene is stirred at 145° C. over 19 hours. The reaction mixture is concentrated by evaporation, the residue is taken up in 12.5 ml of 40:10:1 dichloromethane-methanol-25% conc. ammonia and stirred at room temperature over 1 hour. The mixture is concentrated by evaporation. The title compound is obtained as a yellow resin from the residue by means of flash chromatography (SiO2 60F). Rf=0.65 (40:10:1 dichloromethane-methanol-25% conc. ammonia); Rt=5.61.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. concentrationThe mixture is concentrated by evaporation

Sources & evidence

ORD record
ord-e5e2a653385840afaafd9dbeec205ef4
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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