Hydrochloric Acid → 5-fluoro-1-(piperazin-1-ylmethyl)-2,3-dihydro-1H-indene-4-carbonitrile

HRID 1187038Notes

Reaction equation

HRID 1187038 reaction equation
CC([CH:5]1[CH2:10][N:9]([CH2:11][CH:12]2[C:20]3[C:15](=[C:16]([C:22]#[N:23])[C:17]([F:21])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:8][CH2:7][N:6]1C([O-])=O)(C)C.Cl>C(Cl)Cl>[F:21][C:17]1[CH:18]=[CH:19][C:20]2[CH:12]([CH2:11][N:9]3[CH2:8][CH2:7][NH:6][CH2:5][CH2:10]3)[CH2:13][CH2:14][C:15]=2[C:16]=1[C:22]#[N:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866473161,1-dimethylethyl-4-[(4-cyano-5-fluoro-2,3-dihydro-1H-inden-1-yl)methyl]piperazine-1-carboxylate

Product 1

HCID 595686755-fluoro-1-(piperazin-1-ylmethyl)-2,3-dihydro-1H-indene-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution 1,1-dimethylethyl-4-[(4-cyano-5-fluoro-2,3-dihydro-1H-inden-1-yl)methyl]piperazine-1-carboxylate (0.060 g) in DCM (2 mL) was added 4N HCl (2 mL) at RT. The mixture was allowed to stir at RT for 2 hours. The solvents were removed on a rotary evaporator, and the residue was redissolved in aq NaHCO3 solution. The solution was extracted with IPA-CHCl3 (3:1) twice (50 mL each). The extractions were combined, dried over sodium sulfate, and concentrated to give 5-fluoro-1-(piperazin-1-ylmethyl)-2,3-dihydro-1H-indene-4-carbonitrile. LC-MS (IE, m/z): 260 [M+1]+.

Workup

  1. customThe solvents were removed on a rotary evaporator
  2. dissolutionthe residue was redissolved in aq NaHCO3 solution
  3. extractionThe solution was extracted with IPA-CHCl3 (3:1) twice (50 mL each)
  4. extractionThe extractions
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-22b75f2da26148fc8fddda87d6504608
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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