Diethyl Ether → (S)-6-morpholin-4-yl-4,5,6,7-tetrahydro-benzothiazol-2-ylamine dihydrobromide

HRID 418351Notes

Reaction equation

HRID 418351 reaction equation
C(OC(=O)[NH:10][C:11]1[S:12][C:13]2[CH2:19][C@@H:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH2:17][CH2:16][C:14]=2[N:15]=1)C1C=CC=CC=1.CCOCC.[BrH:32].CC(O)=O>>[BrH:32].[BrH:32].[N:20]1([C@H:18]2[CH2:17][CH2:16][C:14]3[N:15]=[C:11]([NH2:10])[S:12][C:13]=3[CH2:19]2)[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 59190810((s)-6-Morpholin-4-yl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-carbamic acid benzyl ester

Product 1

HCID 86672750(S)-6-morpholin-4-yl-4,5,6,7-tetrahydro-benzothiazol-2-ylamine dihydrobromide

Procedure

Dissolved ((S)-6-morpholin-4-yl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-carbamic acid benzyl ester (7.46 g, 20.00 mmol) in 25 mL of 33% HBr/AcOH. Stirred mixture for 48 h. LC-MS indicated complete deprotection. Added 200 mL of Et2O resulting in a pale orange ppt. Filtered to give 7.46 mg of (S)-6-Morpholin-4-yl-4,5,6,7-tetrahydro-benzothiazol-2-ylaminedihydrobromide a light brown solid.

Workup

  1. filtrationFiltered

Sources & evidence

ORD record
ord-a3fe68b64fab4c7eaa21ca44dc56b565
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Reaction notes

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