HCID 21551659, compound → HCID 21551677, compound

HRID 268401Notes

Reaction equation

HRID 268401 reaction equation
[C:1]1([O:11][CH2:12][CH:13]([OH:30])[CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N+:27]([O-])=O)[CH2:17][CH2:16]2)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.Cl.C1(OCC(O)CN2CCN(C3C=CC=CC=3N)CC2)C2CCCCC=2C=CC=1>O1CCCC1.[Ni]>[C:1]1([O:11][CH2:12][CH:13]([OH:30])[CH2:14][N:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[NH2:27])[CH2:19][CH2:20]2)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 21551659HCID 21551659, compoundHCID 21551680HCID 21551680, compound

Product 1

HCID 21551677HCID 21551677, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

20.6 g. (50 mMole) 1-[3-(5,6,7,8-tetrahydronaphth-1-yloxy)-2-hydroxy-prop-1-yl]-4-(2-nitrophenyl)-piperazine (prepared in the manner described in Example 9) were hydrogenated in tetrahydrofuran, in the presence of Raney nickel in a manner analogous to that described in Example 7. There were thus obtained 19.4 g. (85% of theory) 1-[3-(5,6,7,8-tetrahydronaphth-1-yloxy)-2-hydroxy-prop-1-yl]-4-(2-aminophenyl)-piperazine dihydrochloride, which has a melting point of 268°-271°C. The free base obtained herefrom in the usual manner melts at 103°-104°C.

Workup

  1. customThe free base obtained herefrom in the usual manner melts at 103°-104°C.

Sources & evidence

ORD record
ord-6a775326e93c4d9e9dda19c007a47768
Source dataset
uspto-grants-1976_03
Patent number
US03947446

Reaction notes

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