Lithium hydroxide, monohydrate → HCID 58495461, compound

HRID 1191141Notes

Reaction equation

HRID 1191141 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8](C(=O)C(F)(F)F)[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][S:28]([CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])(=[O:30])=[O:29])=[CH:23][CH:22]=1.O[Li].O>CO>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][S:28]([CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])(=[O:30])=[O:29])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86624181HCID 86624181, compound

Product 1

HCID 58495461HCID 58495461, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 7-chloro-6-[4-(2,2-dimethyl-propanesulfonylmethyl)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (605 mg, 1.14 mmol) in methanol (8 mL) and add LiOH H2O (478 mg, 11.4 mmol). Stir the reaction mixture overnight. Partition the mixture between water and chloroform. Extract the aqueous phase three times with chloroform and chloroform/iso-propanol (3:1). Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel (40 g) eluting with DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) (1:0 over 5 min, 19:1 over 5 min, 9:1; 50 mL/min) to obtain 7-chloro-6-[4-(2,2-dimethyl-propanesulfonylmethyl)-benzylamino]-2,3,4,5-tetrahydro-1H-benzo[d]azepine (467 mg, 94%). MS (APCI+) m/z: 435 (M+H)+.

Workup

  1. customPartition the mixture between water and chloroform
  2. extractionExtract the aqueous phase three times with chloroform and chloroform/iso-propanol (3:1)
  3. dry with materialDry the combined organic extracts over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography on silica gel (40 g)
  7. washeluting with DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) (1:0 over 5 min, 19:1 over 5 min, 9:1; 50 mL/min)

Sources & evidence

ORD record
ord-7bcfa4f7bbb542879ece368af5109b57
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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