Methanol → 1-[3-(5-Chloro-thiophen-2-yl)-4-(tetrahydro-pyran-4-yloxy)-phenyl]-ethylamine

HRID 1098767Notes

Reaction equation

HRID 1098767 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]([C:20](=O)[CH3:21])[CH:10]=[CH:11][C:12]=2[O:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:4][CH:3]=1.CO.C([BH3-])#[N:26].[Na+].FC(F)(F)C(O)=O>>[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]([CH:20]([NH2:26])[CH3:21])[CH:10]=[CH:11][C:12]=2[O:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 59506307HCID 59506307, compound

Product 1

HCID 595062701-[3-(5-Chloro-thiophen-2-yl)-4-(tetrahydro-pyran-4-yloxy)-phenyl]-ethylamine

Procedure

To a solution of the compound yielded from step 2 (1.20 g, 3.56 mmol) in MeOH (20 mL) ammonium acetate (2.75 g, 35.63 mmol) and sodium cyanoborohydride (224 mg, 3.56 mmol) were added. The reaction mixture was refluxed for 6 h. Then the cooled mixture was adjusted with trifluoroacetic acid to pH=2 and evaporated to dryness. Purification of the crude product by prep-HPLC and lyophilization of the relevant fractions lead to the desired product (420 mg, 26%).

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. customevaporated to dryness
  3. customPurification of the crude product by prep-HPLC and lyophilization of the relevant fractions

Sources & evidence

ORD record
ord-8af7bb2dfb5d4981bbfe0b0a7a0ce6f1
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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