Methylamine → HCID 12951846, compound

HRID 1248793Notes

Reaction equation

HRID 1248793 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 2N 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.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. customthe residue partitioned between 2N 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-0621290da763405cb94f9ee845337c4b
Source dataset
uspto-grants-1986_12
Patent number
US04626522

Reaction notes

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