Propylamine → HCID 20570829, compound

HRID 1577515Notes

Reaction equation

HRID 1577515 reaction equation
[OH:1][CH:2](CN1CCC(COC2C=CC=CC=2)CC1)COC1C=CC(C)=C([N+]([O-])=O)C=1[N+]([O-])=O.C(N)CC.[OH:37][CH:38]([CH2:55][N:56]1[CH2:61][CH2:60][CH:59]([CH2:62][O:63][C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[CH2:58][CH2:57]1)[CH2:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[C:43]([N+:48]([O-])=O)[C:42]=1[NH:51][CH2:52][CH2:53][CH3:54]>[Pt]=O>[OH:37][CH:38]([CH2:55][N:56]1[CH2:61][CH2:60][CH:59]([CH2:62][O:63][C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[CH2:58][CH2:57]1)[CH2:39][O:40][C:41]1[C:42]2[N:51]([CH2:52][CH2:53][CH3:54])[C:2](=[O:1])[NH:48][C:43]=2[C:44]([CH3:47])=[CH:45][CH:46]=1

Participants

5

Reactant 3

HCID 7852PropylamineHCID 20570874HCID 20570874, compoundHCID 20570882HCID 20570882, compound

Product 1

HCID 20570829HCID 20570829, compound

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

15.0 g. 1-[2-hydroxy-3-(4-phenoxymethylpiperidino)-propoxy]-4-methyl-2,3-dinitrobenzene (see preparation of the starting material for Example (4a) are heated under reflux in 12 ml. n-propylamine for 3.5 hours. After cooling, there are isolated 8.8 g. (59% of theory) crystalline 1-[2-hydroxy-3-(4-phenoxymethylpiperidino)-propoxy]-4-methyl-2-propylamino-3-nitrobenzene; m.p. 91°-93° C. This compound is hydrogenated in the presence of platinum oxide to give the desired 3-amino-1-[2-hydroxy-3-(4-phenoxymethylpiperidino)-propoxy]-4-methyl-2-propylaminobenzene.

Workup

  1. custompreparation of the starting material for Example (4a)
  2. temperatureare heated
  3. temperatureunder reflux in 12 ml
  4. temperatureAfter cooling
  5. customthere are isolated 8.8 g

Sources & evidence

ORD record
ord-09c61c5b4a2d4f63a8fe42ff243850c8
Source dataset
uspto-grants-1981_09
Patent number
US04288442

Reaction notes

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