참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Sodium hydride | HCID 24758 | — |
| 반응물 | 2-Chloro-4-fluoro-1-nitrobenzene | HCID 75017 | — |
| 반응물 | Tert-butyl 4-hydroxypiperidine-1-carboxylate | HCID 643502 | — |
| 반응물 | Tert-butyl 4-(3-(4-amino-5-chloro-2-methylphenoxy)propyl)piperazine-1-carboxylate | HCID 59349545 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 생성물 | HCID 59349565 | HCID 59349565 | — |
| 생성물 | 1,1-Dimethylethyl 4-(4-amino-3-chlorophenoxy)-1-piperidinecarboxylate | HCID 59349578 | — |
반응 단계
tert-Butyl 4-(4-amino-3-chlorophenoxy)piperidine-1-carboxylate was prepared in the same manner as tert-Butyl 4-(3-(4-amino-5-chloro-2 methylphenoxy)propyl)piperazine-1-carboxylate. Reaction of N-Boc-4-hydroxypiperidine with sodium hydride in anhydrous THF, followed by 2-chloro-4-fluoro-1-nitrobenzene (commercially available from Acros) gave tert-butyl 4-(3-chloro-4-nitrophenoxy)piperidine-1-carboxylate. Reduction of the tent-butyl 4-(3-chloro-4-nitrophenoxy)piperidine-1-carboxylate using ammonium formate and iron dust in refluxing toluene-water mixture gave tert-butyl 4-(4-amino-3-chlorophenoxy)piperidine-1-carboxylate in 79% yield. 1H-NMR (400 MHz, CDCl3): δ 6.88 (m, 1H), 6.70 (m, 2H), 4.26 (m, 1H), 3.79 (s, br, 2H), 3.68 (m, 2H), 3.30 (m, 2H), 1.86 (m, 2H), 1.71 (m, 2H), 1.56 (s, 9H). MS (EI): 227 (MH+).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08088767B2 |
|---|
| 출처 데이터셋 | uspto-grants-2012_01 |
|---|
| ORD ID | ord-3f339d4a163a426ca945d64b95ab6383 |
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| 출처 메모 | uspto-grants-2012_01 |
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