Methylamine → HCID 12951846, compound

HRID 2058658Notes

Reaction equation

HRID 2058658 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[CH2:9][CH2:10][NH:11][CH3:12])=[CH:4][CH:3]=1.B.C1COCC1.ClO.CN.CC1(C)CCCC(C)(C)N1.[F:34][C:35]1[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=1[CH2:37]Cl>C(O)C.C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:13])[CH2:9][CH2:10][N:11]([CH2:37][C:36]2[CH:39]=[CH:40][CH:41]=[CH:42][C:35]=2[F:34])[CH3:12])=[CH:6][CH:7]=1

Participants

9

Reactant 6

HCID 6329MethylamineHCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 130352,2,6,6-TetramethylpiperidineHCID 24341Hypochlorous AcidHCID 2723981Borane;tetrahydrofuranHCID 54324935HCID 54324935, compound

Product 1

HCID 12951846HCID 12951846, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(4-chlorophenyl)-3-hydroxy-N-methylpropylamine (prepared by borane-THF reduction of β-p-dichloropropiophenone followed by reaction of the resulting chloro-alcohol with methylamine in ethanol) (10 g, 50 mmM), 2,2,6,6-tetramethylpiperidine (8.4 ml, 50 mM), o-fluorobenzyl chloride (7.25 g, 50 mM) and acetonitrile (100 ml) was stirred for 24 hours at ambient temperature. The mixture was filtered, the filtrate evaporated and the residue partitioned between 2 N hydrochloric acid and ether. The aqueous layer was basified and extracted with dichloromethane. The organic phase was dried, evaporated and the residue recrystallised from 60°-80° petrol to give the title compound (8.8 g) m.p. 52°-4° C. Found: C, 66.0; H, 6.2; N, 4.4%; C17H19ClFNO requires: C, 66.3; H, 6.2; N, 4.6%.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. customthe residue partitioned between 2 N hydrochloric acid and ether
  4. extractionextracted with dichloromethane
  5. customThe organic phase was dried
  6. customevaporated
  7. customthe residue recrystallised from 60°-80° petrol

Sources & evidence

ORD record
ord-71da25ea83ff43b8a67c78415f17cc31
Source dataset
uspto-grants-1982_03
Patent number
US04318909

Reaction notes

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