HCID 21182733, compound → HCID 21182797, compound

HRID 1387012Notes

Reaction equation

HRID 1387012 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:42]=[CH:41][C:13]([C:14]([C:16]3[C:17]4[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][C:18]=4[S:19][C:20]=3[C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:23][CH:22]=3)=[O:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:40][CH2:39][C:36]1[CH:37]=[CH:38][C:17]2[C:16]([CH:14]([C:13]3[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:42][CH:41]=3)[OH:15])=[C:20]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:25][CH:26]=3)[S:19][C:18]=2[CH:35]=1

Participants

4

Reactant 2

HCID 21182733HCID 21182733, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21182797HCID 21182797, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.35 g (2.3 mol) of 3-[4-[2-(1-piperidinyl)ethoxy]benzoyl]-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene-6-carbonitrile (Part A) in 30 mL of anhydrous THF under a nitrogen atmosphere was added 414 mg (11.6 mmol) of lithium aluminum hydride. The reaction was stirred for 2.5 hours at room temperature and then quenched with 5 mL of ethyl acetate and 5 mL of saturated aqueous potassium sodium tartrate for 16 h. The reaction mixture was poured into 50 mL of water, saturated with sodium chloride, and extracted with three 50 mL portions of THF. The combined organic layers were washed with brine, dried with anhydrous magnesium sulfate, and concentrated to give 1.32 g (95% crude yield) of a brown foam.

Workup

  1. customquenched with 5 mL of ethyl acetate and 5 mL of saturated aqueous potassium sodium tartrate for 16 h
  2. additionThe reaction mixture was poured into 50 mL of water, saturated with sodium chloride
  3. extractionextracted with three 50 mL portions of THF
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto give 1.32 g (95% crude yield) of a brown foam

Sources & evidence

ORD record
ord-7b95d45f35944d5f8f75e18edd839eeb
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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