4-chloro-N-methylpiperidine → HCID 20382083, compound

HRID 1763259Notes

Reaction equation

HRID 1763259 reaction equation
[Mg].Cl[CH:3]1[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1.[Cl:10][C:11]1[C:16]2[CH:17]=[N:18][N:19]([CH2:20][CH3:21])[C:15]=2[N:14]=[C:13]2[C:22](=[O:31])[C:23]3[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=3[CH2:25][CH2:26][C:12]=12>O1CCCC1>[Cl:10][C:11]1[C:16]2[CH:17]=[N:18][N:19]([CH2:20][CH3:21])[C:15]=2[N:14]=[C:13]2[C:22]([CH:3]3[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]3)([OH:31])[C:23]3[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=3[CH2:25][CH2:26][C:12]=12

Participants

5

Reactant 3

HCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 203820734-chloro-1-ethyl-5,6-dihydrobenzo[5,6]-cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11(1H)-one

Product 1

HCID 20382083HCID 20382083, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard reagent is prepared from 7.2 g. of magnesium turnings (0.3 mol.), 230 ml. of dry tetrahydrofuran and 40 g. of 4-chloro-1-methyl-piperidine (0.3 mol.). To this Grignard solution 31 g. of 4-chloro-1-ethyl-5,6-dihydrobenzo[5,6]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11(1H)-one (0.1 mol.), from example 1(e), dissolved in 230 ml. of dry tetrahydrofuran is added. Reaction and work-up according to the procedure of example 15 yields 4-chloro-1-ethyl-1,5,6,11-tetrahydro-11-(1-methyl-4-piperidinyl)benzo[5,6]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11-ol; m.p. 130°-132° (hexane, refrigerator).

Workup

  1. customReaction

Sources & evidence

ORD record
ord-c9af92d75de14f9cbcdd2a9d06497601
Source dataset
uspto-grants-1978_09
Patent number
US04111940

Reaction notes

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