N,N,N',N'-Tetramethylmethanediamine → 2-Dimethylaminomethyl-5-trifluoromethoxy-indan-1-one hydrochloride

HRID 2060070Notes

Reaction equation

HRID 2060070 reaction equation
[CH3:1][N:2]([CH2:4]N(C)C)[CH3:3].[F:8][C:9]([F:22])([F:21])[O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[C:16](=[O:20])[CH2:15][CH2:14]2.C([Cl:26])(=O)C>C(#N)C>[ClH:26].[CH3:1][N:2]([CH2:4][CH:15]1[CH2:14][C:13]2[C:17](=[CH:18][CH:19]=[C:11]([O:10][C:9]([F:22])([F:8])[F:21])[CH:12]=2)[C:16]1=[O:20])[CH3:3]

Participants

5

Reactant 3

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6367Acetyl chlorideHCID 221190265-(Trifluoromethoxy)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 694507812-Dimethylaminomethyl-5-trifluoromethoxy-indan-1-one hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

6.4 ml of bis-(dimethylamino)-methane were added to a solution of 10.1 g of the product from step 2 in 37 ml of acetonitrile; 3.3 ml of acetic acid chloride were added dropwise at from 0 to 10° C., a further 25 ml of acetonitrile were added, and stirring was carried out for 3 hours at 50° C. and then for 18 hours at room temperature. The resulting solid was filtered off with suction, washed twice with diethyl ether and dried in vacuo (yield 12.4 g).

Workup

  1. waitfor 18 hours at room temperature
  2. filtrationThe resulting solid was filtered off with suction
  3. washwashed twice with diethyl ether
  4. customdried in vacuo (yield 12.4 g)

Sources & evidence

ORD record
ord-cc2de47fedfc49518a008117ab77328c
Source dataset
uspto-grants-2012_10
Patent number
US08278338B2

Reaction notes

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