Hydrochloric Acid → HCID 86727094, compound

HRID 1502098Notes

Reaction equation

HRID 1502098 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[O:14][CH2:13][C@H:12]3[CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][CH2:18][N:11]3[CH2:10]2)=[CH:5][C:4]=1[O:26][CH3:27])#[N:2].[ClH:28]>O1CCOCC1>[ClH:28].[CH3:27][O:26][C:4]1[CH:5]=[C:6]([C@H:9]2[O:14][CH2:13][C@H:12]3[CH2:15][NH:16][CH2:17][CH2:18][N:11]3[CH2:10]2)[CH:7]=[CH:8][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71273530HCID 71273530, compound

Product 1

HCID 86727094HCID 86727094, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl (3R,9aR)-3-(4-cyano-3-methoxyphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate (120 mg, 0.321 mmol) was dissolved in 10 Ml of 4 M HCl in dioxane and stirred at room temperature for 8 h. The mixture was concentrated to ¼ the original volume and diluted with 10 Ml of diethyl ether. The precipitate was filtered and dried under high vacuum to offer amine HCl salt: NMR (DMSO-d6, Z (cis) isomer, 500 MHz) δ 7.77 (d, J=7.9 Hz, 1H), 7.32 (s, 1H), 7.19 (d, J=7.9 Hz, 1H), 4.95 (bs, 1H), 4.08 (bs, 2H), 3.96 (s, 3H), 3.85-3.60 (bs, 3H), 3.58-3.34 (m, 6H); LC/MS: (IE, m/z) [M+1]+=274.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with 10 Ml of diethyl ether
  3. filtrationThe precipitate was filtered
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-7cf74f562515491f9eef96acb930410a
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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